Substituted triazoles imidazoles and pyrazoles as herbicides

ABSTRACT

The present invention relates to novel heterocyclic compounds and their agronomically suitable salts, methods for the use of these compounds in controlling unwanted plant species, and the use of herbicidal compositions containing these compounds. In particular, the present invention pertains to substituted and unsubstituted triazoles, imidazoles and pyrazoles linked to a heterocyclic substituted benzene group. Such compounds are useful as pre-emergent and post-emergent herbicides.

This application claims benefit of provisional application 60/139,152 filed Jun. 14, 1999.

The present invention relates to novel heterocyclic compounds and their agronomically suitable salts, methods for the use of these compounds in controlling unwanted plant species, and the use of herbicidal compositions containing these compounds.

The presence of unwanted plant species causes substantial damage to useful crops, especially agricultural products that satisfy the human being's basic food and fiber needs, such as cotton, rice, corn, wheat, soybean. The current population explosion and concomitant world food and fiber shortage demand improvements in efficiency of producing these crops. Prevention or minimizing loss of a portion of such valuable crops by killing, or inhibiting the growth of unwanted plant species is one way of improving this efficiency. Though many herbicides are available, the need still exists for more effective herbicides.

The compounds of the present invention in general show a usefully improved level of crop safety on soybean, corn or wheat than the known compounds.

EP 0 083 055 A2, published Jul. 6, 1983, discloses herbicidal compounds of the following formula (i)

wherein

R₁ is hydrogen, alkyl, lower cycloalkyl, lower alkyl(lower)cycloalkyl, lowercycloalkyl(lower)alkyl, lower alkoxyl(lower)alkyl, lower alkenyl, lower cycloalkenyl, lower cycloalkenyl(lower)alkyl, phenyl, cyano(lower)alkyl, lower alkynyl, lower alkylideneamino, lower alkylthio(lower)alkyl, benzyl, halo(lower)alkyl or lower cycloalkylideneamino;

R₂ is hydrogen, lower alkyl, lower alkoxyl;

X is chlorine or bromine;

Y is oxygen or imino; and

Z is oxygen or sulfur.

EP 0 273 417 A1 published Jul. 6, 1988 discloses the herbicidal compounds having the formula (ii)

wherein

each of X and Y is hydrogen or halogen;

Z is —SCH(R)COOR¹;

R is hydrogen, alkyl, and R¹ is alkyl, cycloalkyl, or alkoxyalkyl, or COOQ wherein Q is alkyl, or Y and Z together form

bonded to phenyl ring, wherein R² is H or alkyl, and R³ is alkyl, alkenyl, or alkynyl.

The present invention relates to novel herbicidal compounds and methods for their use in controlling unwanted plant species and their use in herbicidal compositions in agriculture. In particular, the present invention pertains to substituted and unsubstituted triazoles, imidazoles and pyrazoles linked to a heterocyclic substituted benzene group.

It has now been found that certain triazoles, imidazoles and pyrazoles linked to a heterocyclic substituted benzene group are useful as pre-emergent and post-emergent herbicides. These novel compounds are represented by formula I

wherein

R₁ is selected from H, F, Br, Cl, NO₂ and CN;

R₂ is selected from F, Cl, Br, H and CN;

R₃ is selected from H and CN; and alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, cycloalkenyl, haloalkenyl, haloalkynyl, alkoxy, alkylthio, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl, aryl, arylalkyl, heteroaryl and heteroarylalkyl, all of which may be further substituted;

R₄ and R₅ are each independently selected from H, halo and CN; and alkyl, cycloalkyl, haloalkyl, alkoxy, alkylthio, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl, CO₂R₆, CONR₆R₁₃, OR₆, SR₆, SO₂R₆, NR₆R₁₃, SO₂NR₆R₁₃, aryl, arylalkyl, heteroaryl and heteroarylalkyl, all of which may be further substituted;

R₆ is selected from H, alkyl, cycloalkyl, alkoxy, alkylthio, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl, aryl and arylalkyl, all of which may be further substituted;

R₇ is selected from H, alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl and COR₉, all of which may be further substituted;

R₈ is selected from alkyl, haloalkyl, cycloalkyl, cycloalkenyl, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl, aryl and arylalkyl, all of which may be further substituted;

R₉ is selected from H, alkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl, alkenyl, alkynyl, haloalkyl and cycloalkyl, all of which may be further substituted;

R₁₀ is selected from H, halo, NH₂, alkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl, haloalkyl, CN, CO₂(alkyl), CONH(alkyl), CON(alkyl)₂ wherein each alkyl may be the same or different, CH₂CN, CH₂CH═CH₂, CH₂C≡CH, CH₂CO₂(alkyl), CH₂OCH₃ and CH₂-1,2,4-triazole, all of which may be further substituted;

R₁₁ is selected from H, CN, alkyl, haloalkyl and CO₂(alkyl);

R₁₂ is selected from H, alkyl, CO₂R₆, CONR₆R₁₃, OR₆, SR₆, SO₂R₆, SO₂NR₆R₁₃ and NR₆R₁₃;

R₁₃ is H, alkyl, aryl or arylalkyl;

A is N or CH;

B is N or CR₁₀;

Z is O, CH(R₃), CO, CS, CONR₁₂ or CSNR₁₂;

X is selected from O, S, NR₁₂, CO₂, OCH(R₆)CO₂, SCH(R₆)CO₂, CH═C(halo)CO₂, CH₂CH(halo)CO₂, CONH, OCH(R₆)CONH, SCH(R₆)CONH, CH═C(halo)CONH and CH₂CH(halo)CONH when Z is CH(R₃);

X is selected from CO, OCH(R₆)CO, SCH(R₆)CO, CH═C(halo)CO and CH₂CH(halo)CO when Z is O;

X is selected from O, S, CO, OCH(R₆), CH═C(halo), CH₂CH(halo), CONH, OCH(R₆)CONH, SCH(R₆)CONH, CH═C(halo)CONH, CH₂CH(halo)CONH and NR₁₂ when Z is CO, CS, CONR₁₂ or CSNR₁₂; and

Q is selected from NR₇COR₈, Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q14, Q15 and Q16 wherein

Q1 is 4,5,6,7-tetrahydrophthalimid-2-yl,

Q2 is 5,6,7,8-tetrahydro-1,2,4-triazolo[4, 3-a]pyridin-3(2H)-one-1-yl,

Q3 is 5,6,7,8-tetrahydro-1H,3H-[1,3,4]thiadiazolo[3,5-a]pyridazineimin-1-yl,

Q4 is 4,5,6,7-tetrahydroimidazo[1,5-a]pyridine-1,3(2H,5H)-dione-2-yl,

Q5 is 1,6,8-triazabicyclo[4,3,0]-nonane-7,9-dion-8-yl,

Q6 is 5-(1-methyethylidene)-2,4-oxazolidinedione-3-yl,

Q7 is 5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2(3H)-one-3-yl,

Q8 is 4-difluoromethyl-4, 5-dihydro-3-methyl- 1,2,4-triazol-5(1H)-one-1-yl,

Q9 is 2-methyl-1,2,4-oxadiazolidine-3,5-dione-4-yl,

Q10 is 4-chloro-1-methyl-5-difluoromethoxy-1H-pyrazol-3-yl,

Q11 is 4-bromo-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl,

Q12 is 1-substituted-6-trifluoromethyl-2,4-pyrimidione-3-yl,

Q13 is 1-substituted-6-trifluoromethyl-1,3,5-triazine-2,4-dione-1-yl,

Q14 is 4,5-disubstituted-4,5-dihydro-1,2,4-triazine-3(2H)-one-2-yl,

Q15 is 4-substituted-1,2,4-triazine-3,5(2H,4H)-dione-2-yl and

Q16 is 5-methyl-6-oxo-4-(trifluoromethyl)-6H-pyridazin- 1-yl;

or the agronomically acceptable salts thereof

As used in the present invention, the term “aryl” is defined as a monocyclic or polycyclic ring selected from benzene, naphthalene, indene, anthracene, indacene, fluorene, acenaphthalene, phenanthrene and azulene.

“Heteroaryl” is defined as a monocyclic or polycyclic ring selected from furan, thiophene, pyrrole, isoxazole, oxazole, isothiazole, thiazole, pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, tetrazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,3,4-thiadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,3,4-thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,4,5-tetrazine, benzofuran, benzothiophene, indole, benzisoxazole, benzoxazole, benzisothiazole, benzothiazole, benzopyrazole, benzimidazole, benzotriazole, 1,2-methylenedioxybenzene, 1,2-ethylenedioxybenzene, quinoline and isoquinoline.

The structures of the “Q” heterocyclic groups previously named are

where R₁₀ and R₁₁ are as previously defined.

The term “alkyl” includes both branched and straight chain alkyl groups. Typical alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, isooctyl, nonyl, decyl, undecyl, dodecyl and the like.

The term “cycloalkyl” refers to a cyclic aliphatic ring structure such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane and the like.

The term “haloalkyl” refers to an alkyl group substituted with one or more halo groups.

The term “halo” refers to fluoro, chloro, bromo or iodo.

The term “alkylsulfonylalkyl” refers to an alkyl group substituted with an alkylsulfonyl (alkyl-SO₂) group, for example methylsulfonylmethyl.

The term “alkylsulfinylalkyl” refers to an alkyl group substituted with an alkylsulfinyl (alkyl-SO) group, for example methylsulfinylmethyl.

The term “alkenyl” refers to an ethylenically unsaturated hydrocarbon group, straight or branched, having 1 or 2 ethylenic bonds.

The term “cycloalkenyl” refers to a cyclic aliphatic ring structure having 1 or 2 ethylenic bonds such as cyclopentene, cyclohexene, 1,4-cyclohexadiene and the like.

The term “haloalkenyl” refers to an alkenyl group substituted with one or more halo groups.

The term “alkynyl” refers to an unsaturated hydrocarbon group, straight or branched, having 1 or 2 acetylenic bonds.

The term “arylalkyl” is used to describe a group wherein the alkyl chain can be branched or straight chain with the aryl portion, as defined above, forming a terminal portion of the arylalkyl moiety.

The term “heteroarylalkyl” is used to describe a group wherein the alkyl chain can be branched or straight chain with the heteroaryl portion, as defined above, forming a terminal portion of the heteroarylalkyl moiety.

The term “alkoxy” includes both branched and straight chain alkyl groups attached to a terminal oxygen atom. Typical alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy and the like.

The term “haloalkoxy” refers to an alkoxy group substituted with one or more halo groups.

The term “alkylthio” includes both branched and straight chain alkyl groups attached to a terminal sulfur atom.

The term “haloalkylthio” refers to an alkylthio group substituted with one or more halo groups.

Acceptable acids that may form salts of the compounds of the present invention can be selected from hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, phosphoric acid, oxalic acid, acetic acid, propionic acid, glycolic acid, methanesulfonic acid, toluenesulfonic acid, benzenesulfonic acid, (C₂-C₂₀)alkylbenzenesulfonic acid, sodium hydrogen sulfate and methyl hydrogen sulfate.

Other agronomically acceptable salts may be formed by complexation of the compounds of the current invention with metal salts such as zinc chloride or iron chloride.

A preferred embodiment of this invention are the compounds of formula I wherein

R₁ is selected from H, F, Br, Cl, NO₂ and CN;

R₂ is selected from F, Cl, Br, H and CN;

R₃ is selected from H, CN and halo; and (C₁-C₁₂)alkyl, cyclo(C₃-C₈)alkyl, (C₂-C₁₂)alkenyl, cyclo(C₃-C₈)alkenyl, (C₂-C₁₂)alkynyl, halo(C₁-C₁₂)alkyl, halo(C₂-C₁₂)alkenyl, halo(C₂-C₁₂)alkynyl, (C₁-C₁₂)alkoxy, (C₁-C₁₂)alkylthio, (C₁-C₁₂)alkylsulfonyl(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfinyl(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfonylcyclo(C₃-C₈)alkyl, (C₁-C₁₂)alkylsulfinylcyclo(C₃-C₈)alkyl, cyano(C₁-C₁₂)alkoxy, cyano(C₁-C₁₂)alkyl, cyanocyclo(C₃-C₈)alkyl, halo(C₁-C₁₂)alkoxy, halo(C₁-C₁₂)alkylthio, halocyclo(C₃-C₈)alkyl, aryl, heteroaryl, aryl(C₁-C₁₂)alkyl and heteroaryl(C₂-C₁₂)alkyl, all of which may be further substituted with from one to three substituents independently selected from bromo, chloro, fluoro, (C₁-C₁₂)alkyl, cyclo(C₃-C₈)alkyl, (C₂-C₁₂)alkenyl, cyclo(C₃-C₈)alkenyl, (C₂-C₁₂)alkynyl, halo(C₁-C₁₂)alkyl, halo(C₂-C₁₂)alkenyl, halo(C₂-C₁₂)alkynyl, (C₁-C₁₂)alkoxy, (C₁-C₁₂)alkylthio, (C₁-C₁₂)alkylsulfonyl, (C₁-C₁₂)alkylsulfinyl, phenyl, phen(C₁-C₁₂)alkyl, phen(C₂-C₁₂)alkenyl, phen(C₂-C₁₂)alkynyl, cyano, halo(C₁-C₁₂)alkoxy, 1,3-dioxalan-2-yl and nitro;

R₄ and R₅ are each independently selected from H, halo and CN; and (C₁-C₁₂)alkyl, cyclo(C₃-C₈)alkyl, halo(C₁-C₁₂)alkyl, (C₁-C₁₂)alkoxy, (C₁-C₁₂)alkylthio, (C₁-C₁₂)alkylsulfonyl (C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfinyl(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfonylcyclo(C₃-C₈)alkyl, (C₁-C₁₂)alkylsulfinylcyclo(C₃-C₈)alkyl, cyano(C₁-C₁₂)alkoxy, cyano(C₁-C₁₂)alkyl, cyanocyclo(C₃-C₈)alkyl, halo(C₁-C₁₂)alkoxy, halo(C₁-C₁₂)alkylthio, halocyclo(C₃-C₈)alkyl, CO₂R₆, CONHR₆, CON((C₁-C₁₂)alkyl)R₆, OR₆, SR₆, SO₂R₆, NHR₆, N((C₁-C₁₂)alkyl)R₆, SO₂N((C₁-C₁₂)alkyl)R₆, aryl, heteroaryl, aryl(C₁-C₁₂)alkyl and heteroaryl(C₂-C₁₂)alkyl, all of which may be further substituted with from one to three substituents independently selected from bromo, chloro, fluoro, (C₁-C₁₂)alkyl, cyclo(C₃-C₈)alkyl, (C₂-C₁₂)alkenyl, cyclo(C₃-C₈)alkenyl, (C₂-C₁₂)alkynyl, halo(C₁-C₁₂)alkyl, halo(C₂-C₁₂)alkenyl, halo(C₂-C₁₂)alkynyl, (C₁-C₁₂)alkoxy, (C₁-C₁₂)alkylthio, (C₁-C₁₂)alkylsulfonyl, (C₁-C₁₂)alkylsulfinyl, phenyl, phen(C₁-C₁₂)alkyl, phen(C₂-C₁₂)alkenyl, phen(C₂-C₁₂)alkynyl, cyano, halo(C₁-C₁₂)alkoxy, 1,3-dioxalan-2-yl and nitro;

R₆is selected from H, (C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfonyl(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfinyl(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfonylcyclo(C₃-C₈)alkyl, (C₁-C₁₂)alkylsulfinylcyclo(C₃-C₈)alkyl, cyano(C₁-C₁₂)alkoxy, cyano(C₁-C₁₂)alkyl, cyanocyclo(C₃-C₈)alkyl, halo(C₁-C₁₂)alkoxy, halo(C₁-C₁₂)alkylthio, halocyclo(C₃-C₈)alkyl, aryl and aryl(C₁-C₁₂)alkyl;

R₇ is selected from H, (C₁-C₁₂)alkyl, cyclo(C₃-C₈)alkyl, halo(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfonyl(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfinyl(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfonylcyclo(C₃-C₈)alkyl, (C₁-C₁₂)alkylsulfinylcyclo(C₃-C₈)alkyl, cyano(C₁-C₁₂)alkoxy, cyano(C₁-C₁₂)alkyl, cyanocyclo(C₃-C₈)alkyl, halo(C₁-C₁₂)alkoxy, halo(C₁-C₁₂)alkylthio, halocyclo(C₃-C₈)alkyl and COR₉;

R₈ is selected from (C₁-C₁₂)alkyl, cyclo(C₃-C₈)alkyl, cyclo(C₃-C₈)alkenyl, halo(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfonyl (C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfinyl(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfonylcyclo(C₃-C₈)alkyl, (C₁-C₁₂)alkylsulfinylcyclo(C₃-C₈)alkyl, cyano (C₁-C₁₂)alkoxy, cyano(C₁-C₁₂)alkyl, cyanocyclo(C₃-C₈)alkyl, halo(C₁-C₁₂)alkoxy, halo(C₁-C₁₂)alkylthio, halocyclo(C₃-C₈)alkyl, aryl and aryl(C₁-C₁₂)alkyl;

R₉ is selected from H, (C₁-C₁₂)alkyl, (C₂-C₁₂)alkenyl, cyclo(C₃-C₈)alkyl, halo(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfonyl(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfinyl(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfonylcyclo(C₃-C₈)alkyl, (C₁-C₁₂)alkylsulfinylcyclo(C₃-C₈)alkyl, cyano(C₁-C₁₂)alkoxy, cyano(C₁-C₁₂)alkyl, cyanocyclo(C₃-C₈)alkyl, halo(C₁-C₁₂)alkoxy, halo(C₁-C₁₂)alkylthio and halocyclo(C₃-C₈)alkyl;

R₁₀ is selected from H, chloro, NH₂, (C₁-C₁₂)alkyl, halo(C₁-C₁₂)alkyl, CN, (C₁-C₁₂)alkylsulfonyl(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfinyl(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfonylcyclo(C₃C₈)alkyl, (C₁-C₁₂)alkylsulfinylcyclo(C₃-C₈)alkyl, cyano(C₁-C₁₂)alkoxy, cyano(C₁-C₁₂)alkyl, cyanocyclo(C₃-C₈)alkyl, halo(C₁-C₁₂)alkoxy, halo(C₁-C₁₂)alkylthio, halocyclo(C₃-C₈)alkyl, CO₂(C₁-C₁₂)alkyl, CONH(C₁-C₁₂)alkyl, CON((C₁-C₁₂)alkyl)₂, CH₂CN, CH₂CH═CH₂, CH₂C≡CH, CH₂CO₂(C₁-C₁₂)alkyl, CH₂OCH₃, CH₂-1,2,4-triazole;

R₁₁ is selected from H, CN, (C₁-C₁₂)alkyl, halo(C₁-C,₂)alkyl and CO₂(C₁-C₁₂)alkyl;

R₁₂ is selected from H, (C₁-C₁₂)alkyl, CO₂R₆, CON((C₁-C₁₂)alkyl)R₆, OR₆, SR₆, SO₂R₆, SO₂N((C₁-C₁₂)alkyl)R₁₃ and N((C₁-C₁₂)alkyl)R₁₃;

R₁₃ is H, (C₁-C₁₂)alkyl, aryl or aryl(C₁-C₁₂)alkyl;

A is N or CH;

B is N or CR₁₀;

Z is O, CH(R₃), CO, CS, CONR₁₂ or CSNR₁₂;

X is selected from O, S, NR₁₂, CO₂, OCH(R₆)CO₂, SCH(R₆)CO₂, CH═C(Cl)CO₂, CH₂CH(Cl)CO₂, CONH, OCH(R₆)CONH, SCH(R₆)CONH, CH═C(Cl)CONH and CH₂CH(Cl)CONH when Z is CH(R₃);

X is selected from CO, OCH(R₆)CO, SCH(R₆)CO, CH═C(Cl)CO, CH₂CH(Cl)CO when Z is O;

X is selected from O, S, CO, OCH(R₆), CH═C(Cl), CH₂CH(Cl), CONH, OCH(R₆)CONH, SCH(R₆)CONH, CH═C(Cl)CONH, CH₂CH(Cl)CONH and NR₁₂ when Z is CO, CS, CONR₁₂ or CSNR₁₂;

Q is selected from NR₇COR₈, Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q14, Q15 and Q16;

or the agronomically acceptable salts thereof.

A more preferred embodiment of this invention are the compounds of formula I wherein

R₁ is H, F or Cl;

R₂ is Cl;

R₃ is selected from H, bromo, chloro, fluoro, (C₁-C₆)alkyl, cyclo(C₅-C₆)alkyl, (C₂-C₆)alkenyl, cyclo(C₃-C₈)alkenyl, (C₂-C₆)alkynyl, halo(C₁-C₆)alkyl, halo(C₂-C₆)alkenyl, halo(C₂-C₆)alkynyl, (C₁-C₆)alkoxy, (C₁-C₆)alkylthio, aryl, heteroaryl, aryl(C₁-C₁₂)alkyl and heteroaryl(C₂-C₁₂)alkyl wherein the aryl or heteroaryl group is selected from furan, naphthalene, phenyl, pyrazole, pyridine, pyrimidine, thiophene and triazole, said aryl and heteroaryl group may be further substituted with from one to three substituents independently selected from bromo, chloro, fluoro, (C₁-C₁₂)alkyl, cyclo(C₃-C₈)alkyl, (C₂-C₁₂)alkenyl, cyclo(C₃-C₈)alkenyl, (C₂-C₁₂)alkynyl, halo(C₁-C₁₂)alkyl, halo(C₂-C₁₂)alkenyl, halo(C₂-C₁₂)alkynyl, (C₁-C₁₂)alkoxy, (C₁-C₁₂)alkylthio, (C₁-C₁₂)alkylsulfonyl, (C₁-C₁₂)alkylsulfinyl, phenyl, phen(C₁-C₁₂)alkyl, phen(C₂-C₁₂)alkenyl, phen(C₂-C₁₂)alkynyl, cyano, halo(C₁-C₁₂)alkoxy, 1,3-dioxalan-2-yl and nitro;

R₄ and R₅ are each independently selected from H, bromo, chloro, fluoro, CN, (C₁-C₆)alkyl, cyclo(C₅-C₆)alkyl, halo(C₁-C₆)alkyl, (C₁-C₆)alkoxy, (C₁-C₆)alkylthio, CO₂R₆, CONHR₆, CON((C₁-C₁₂)alkyl)R₆, OR₆, SR₆, SO₂R₆, NHR₆, N((C₁-C₁₂)alkyl)R₆, SO₂N((C₁-C₁₂)alkyl)R₆, aryl, heteroaryl, aryl(C₁-C₁₂)alkyl and heteroaryl(C₂-C₁₂)alkyl, wherein the aryl or heteroaryl group is selected from furan, naphthalene, phenyl, pyrazole, pyridine, pyrimidine, thiophene and triazole, said aryl and heteroaryl group may be further substituted with from one to three substituents independently selected from bromo, chloro, fluoro, (C₁-C₁₂)alkyl, cyclo(C₃-C₈)alkyl, (C₂-C₁₂)alkenyl, cyclo(C₃-C₈)alkenyl, (C₂-C₁₂)alkynyl, halo(C₁-C₁₂)alkyl, halo(C₂-C₁₂)alkenyl, halo(C₂-C₁₂)alkynyl, (C₁-C₁₂)alkoxy, (C₁-C₁₂)alkylthio, (C₁-C₁₂)alkylsulfonyl, (C₁-C₁₂)alkylsulfinyl, phenyl, phen(C₁-C₁₂)alkyl, phen(C₂-C₁₂)alkenyl, phen(C₂-C₁₂)alkynyl, cyano, halo(C₁-C₁₂)alkoxy, 1,3-dioxalan-2-yl and nitro;

R₆ is selected from H, (C₁-C₁₂)alkyl, aryl and aryl(C₁-C₆)alkyl, where the aryl group is naphthyl or phenyl;

R₇ is selected from H, (C₁-C₁₂)alkyl, cyclo(C₃-C₈)alkyl, halo(C₁-C₁₂)alkyl and COR₉;

R₈ is selected from (C₁-C₁₂)alkyl, cyclo(C₃-C₈)alkyl, cyclo(C₃-C₈)alkenyl, halo(C₁-C₁₂)alkyl, aryl and aryl(C₁-C₆)alkyl;

R₉ is selected from H, (C₁-C₆)alkyl, (C₂-C₁₂)alkenyl, (C₂-C₆)alkenyl, cyclo(C₃-C₈)alkyl, cyclo(C₅-C₆)alkyl, halo(C₁-C₁₂)alkyl, halo(C₁-C₆)alkyl;

R₄ is selected from H, chloro, NH₂, (C₁-C₆)alkyl, halo(C₁-C₁₂)alkyl, halo(C₁-C₆)alkyl, CN, CO₂(C₁-C₁₂)alkyl, CONH(C₁-C₁₂)alkyl, CON((C₁-C₁₂)alkyl)₂, CH₂CN, CH₂CH═CH₂, CH₂C≡CH, CH₂CO₂(C₁-C₁₂)alkyl, CH₂OCH₃, CH₂-1,2,4-triazole;

R₁₁ is selected from H, CN, (C₁-C₆)alkyl, halo(C₁-C₁₂)alkyl, halo(C₁-C₆)alkyl and CO₂(C₁-C₁₂)alkyl;

R₁₂ is selected from H, (C₁-C₈)alkyl, CO₂R₆, CON((C₁-C₈)alkyl)R₆, OR₆, SR₆, SO₂R₆, SO₂N((C₁-C₈)alkyl)R₁₃ and N((C₁-C₈)alkyl)R₁₃;

R₁₃ is H, (C₁-C₈)alkyl, aryl or aryl(C₁-C₆)alkyl where the aryl group is naphthyl or phenyl;

A is N or CH;

B is N or CR₁₀;

Z is O, CH(R₃), CO, CS, CONR₁₂ or CSNR₁₂;

X is selected from O, S, NH, CO₂, OCH(R₆)CO₂, SCH(R₆)CO₂, CH═C(Cl)CO₂, CH₂CH(Cl)CO₂, CONH, OCH(R₆)CONH, SCH(R₆)CONH, CH═C(Cl)CONH and CH₂CH(Cl)CONH when Z is CH(R₃);

X is selected from CO, OCH(R₆)CO, SCH(R₆)CO, CH═C(Cl)CO and CH₂CH(Cl)CO when Z is O;

X is selected from O, S, CO, OCH(R₆), CH═C(Cl), CH₂CH(Cl), CONH, OCH(R₆)CONH, SCH(R₆)CONH, CH═C(Cl)CONH, CH₂CH(Cl)CONH and NR₁₂ when Z is CO, CS, CONR₁₂ or CSNR₁₂;

Q is NR₇COR₈, or selected from Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q14, Q15 and Q16;

or the agronomically acceptable salts thereof selected from those formed from hydrochloric acid, sulfuric acid, acetic acid, propionic acid, phosphoric acid and oxalic acid.

An even more preferred embodiment of this invention are the compounds of formula I wherein

R₁ is H, F or Cl;

R₂ is Cl;

R₃ is selected from H, bromo, chloro, fluoro, (C₁-C₆)alkyl, cyclo(C₅-C₆)alkyl, (C₂-C₆)alkenyl, cyclo(C₃-C₈)alkenyl, (C₂-C₆)alkynyl, halo(C₁-C₆)alkyl, halo(C₂-C₆)alkenyl, halo(C₂-C₆)alkynyl, (C₁-C₆)alkoxy, (C₁-C₆)alkylthio, 3-furyl, 4-chloro-2-furyl, 5-chloro-2-furyl, 5-chloro-3-furyl, 2,5-dichloro-3-furyl, 1-naphthyl, 2-naphthyl, phenyl, 4-methylphenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-fluorophenyl, 4-chlorophenyl, 4-trifluoromethylphenyl, 4-bromophenyl, 4-chlorophenyl, 3-fluorophenyl, 4-trifluoromethoxyphenyl, 4-cyanophenyl, 3-(1,3-dioxolan-2-yl)phenyl, 2-fluorophenyl, 2-chlorophenyl, 2-trifluoromethoxyphenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 3-chloro-4-fluorophenyl, 3,4-difluorophenyl, 3-fluoro-5-trifluoromethylphenyl, 3,4,5-trifluorophenyl, 2-pyridyl, 4-chloro-2-pyridyl, 6-chloro-2-pyridyl, 4,6-dichloro-2-pyridyl, 3-pyridyl, 5-bromo-3-pyridyl, 5,6-dichloro-3-pyridyl, 5-chloro-3-pyridyl, 5-fluoro-3-pyridyl, 4-pyridyl, 2-fluoro-4-pyridyl, 2-chloro-4-pyridyl, 2-chloro-6-methyl-4-pyridyl, 2-methyl-4-pyridyl, 2-methoxy-4-pyridyl, 2-cyano-4-pyridyl, 2,6-difluoro-4-pyridyl, 2, 6-dichloro-4-pyridyl, 2-thienyl, 3-thienyl, 4-chloro-2-thienyl, 5-chloro-2-thienyl, 5-chloro-3-thienyl and 2,5-dichloro-3-thienyl;

R₄ and R₅ are each independently selected from H, bromo, chloro, fluoro, CN, (C₁-C₆)alkyl, cyclo(C₅-C₆)alkyl, halo(C₁-C₆)alkyl, (C₁-C₆)alkoxy, (C₁-C₆)alkylthio, CO₂R₆, CONHR₆, CON((C₁-C₆)alkyl)R₆, OR₆, SR₆, SO₂R₆, NHR₆, 3-furyl, 4-chloro-2-furyl, 5-chloro-2-furyl, 5-chloro-3-furyl, 2,5-dichloro-3-furyl, 1-naphthyl, 2-naphthyl, phenyl, 4-methylphenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-fluorophenyl, 4-chlorophenyl, 4-trifluoromethylphenyl, 4-bromophenyl, 4-chlorophenyl, 3-fluorophenyl, 4-trifluoromethoxyphenyl, 4-cyanophenyl, 3-(1,3-dioxolan-2-yl)phenyl, 2-fluorophenyl, 2-chlorophenyl, 2-trifluoromethoxyphenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 3-chloro-4-fluorophenyl, 3,4-difluorophenyl, 3-fluoro-5-trifluoromethylphenyl, 3,4,5-trifluorophenyl, 2-pyridyl, 4-chloro-2-pyridyl, 6-chloro-2-pyridyl, 4,6-dichloro-2-pyridyl, 3-pyridyl, 5-bromo-3-pyridyl, 5,6-dichloro-3-pyridyl, 5-chloro-3-pyridyl, 5-fluoro-3-pyridyl, 4-pyridyl, 2-fluoro-4-pyridyl, 2-chloro-4-pyridyl, 2-chloro-6-methyl-4-pyridyl, 2-methyl-4-pyridyl, 2-methoxy-4-pyridyl, 2-cyano-4-pyridyl, 2,6-difluoro-4-pyridyl 2,6-dichloro-4-pyridyl, 2-thienyl, 3-thienyl, 4-chloro-2-thienyl, 5-chloro-2-thienyl, 5-chloro-3-thienyl and 2,5-dichloro-3-thienyl;

R₆ is selected from H, (C₁-C₆)alkyl, 1-naphthyl, 2-naphthyl, phenyl, 4-methylphenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-fluorophenyl, 4-chlorophenyl, 4-trifluoromethylphenyl, 4-bromophenyl, 4-chlorophenyl, 3-fluorophenyl, 4-trifluoromethoxyphenyl, 4-cyanophenyl, 3-(1,3-dioxolan-2-yl)phenyl, 2-fluorophenyl, 2-chlorophenyl, 2-trifluoromethoxyphenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 3-chloro-4-fluorophenyl, 3,4-difluorophenyl, 3-fluoro-5-trifluoromethylphenyl and 3,4,5-trifluorophenyl;

R₇ is selected from H, (C₁-C₆)alkyl, cyclo(C₅-C₆)alkyl, halo(C₁-C₆)alkyl and COR₉;

R₈ is (C₁-C₆)alkyl, cyclo(C₅-C₆)alkyl, halo(C₁-C₁₂)alkyl, 1-naphthyl, 2-naphthyl, phenyl, 4-methylphenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-fluorophenyl, 4-chlorophenyl, 4-trifluoromethylphenyl, 4-bromophenyl, 4-chlorophenyl, 3-fluorophenyl, 4-trifluoromethoxyphenyl, 4-cyanophenyl, 3-(1,3-dioxolan-2-yl)phenyl, 2-fluorophenyl, 2-chlorophenyl, 2-trifluoromethoxyphenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 3-chloro-4-fluorophenyl, 3,4-difluorophenyl, 3-fluoro-5-trifluoromethylphenyl and 3,4,5-trifluorophenyl;

R₉ is selected from H, (C₁-C₆)alkyl, (C₂-C₆)alkenyl, cyclo(C₅-C₆)alkyl and halo(C₁-C₆)alkyl;

R₁₀ is selected from H, chloro, NH₂, (C₁-C₆)alkyl, halo(C₁-C₆)alkyl, CN, CO₂(C₁-C₆)alkyl, CONH(C₁-C₆)alkyl, CON((C₁-C₆)alkyl)₂, CH₂CN, CH₂CH═CH₂, CH₂C≡CH, CH₂CO₂(C₁-C₆)alkyl, CH₂OCH₃ and CH₂-1,2,4-triazole;

R₁₁ is H, CN, (C₁-C₆)alkyl, halo(C₁-C₆)alkyl and CO₂(C₁-C₆)alkyl;

R₁₂ is selected from H, (C₁-C₆)alkyl, CO₂(C₁-C₆)alkyl, CON((C₁-C₆)alkyl)₂, O(C₁-C₆)alkyl, S(C₁-C₆)alkyl, SO₂(C₁-C₆)alkyl, SO₂N((C₁-C₆)alkyl)₂ and N((C₁-C₆)alkyl)₂;

R₁₃ is H, (C₁-C₆)alkyl, aryl or aryl(C₁-C₄)alkyl where the aryl group is naphthyl or phenyl;

A is N or CH;

B is N or CR₁₀;

Z is O, CH(R₃), CO, CS, CONR₁₂ or CSNR₁₂;

X is selected from O, S, NH, CO₂, OCH(R₆)CO₂, SCH(R₆)CO₂, CH═C(Cl)CO₂, CH₂CH(Cl)CO₂, CONH, OCH(R₆)CONH, SCH(R₆)CONH, CH═C(Cl)CONH and CH₂CH(Cl)CONH when Z is CH(R₃);

X is selected from CO, OCH(R₆)CO, SCH(R₆)CO, CH═C(Cl)CO and CH₂CH(Cl)CO when Z is O;

X is selected from O, S, CO, OCH(R₆), CH═C(Cl), CH₂CH(Cl), CONH, OCH(R₆)CONH, SCH(R₆)CONH, CH═C(Cl)CONH, CH₂CH(Cl)CONH and NR₁₂ when Z is CO, CS, CONR₁₂ or CSNR₁₂;

Q is selected from Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q14, Q15 and Q16;

or the agronomically acceptable salts thereof selected from those formed from hydrochloric acid, acetic acid, phosphoric acid and oxalic acid.

A second aspect of this invention relates to herbicidal compositions comprising a compound of formula I and an agronomically acceptable carrier.

A third aspect of this invention relates to a method of controlling a weed comprising applying a herbicidally effective amount of a composition comprising a compound of formula I and an agronomically acceptable carrier to the weed, to the locus of the weed or to the growth medium of said weed.

The following examples of the compounds of formula I are presented in Tables 5-25 and are representative of the invention. In these tables, the abbreviation “Ph” is used to mean phenyl, “Ph-4-Cl” is used to mean 4-chlorophenyl, “Ph-4-F” is used to mean 4-fluorophenyl, “CH₂Ph” is used to mean benzyl, “CH₂Ph-4-Cl” is used to mean 4-chlorobenzyl, “3-Py” is used to mean 3pyridyl, “Me” is used to mean methyl and “Et” is used to mean ethyl.

TABLE 1

where A = B = N, Q = Q1 in a compound of formula I No R₁ R₂ X R₃ R₄ R₅  1 F Cl CO₂ H H H  2 F Cl CO₂ CH₃ H H  3 F Cl CO₂ C₂H₅ H H  4 F Cl CO₂ C₃H₇ H H  5 F Cl CO₂ H CH₃ CH₃  6 F Cl CO₂ CH₃ Ph CH₃  7 F Cl CO₂ C₂H₅ Ph-4-Cl H  8 F Cl CO₂ H H SCH₃  9 F Cl CO₂ CN H H  10 F Cl CO₂ Ph H H  11 F Cl CO₂ CH₂Ph H H  12 F Cl CO₂ Ph-4-Cl H H  13 F Cl CO₂ CH₂Ph-4-Cl H H  14 F Cl CO₂ 3-Py H H  15 F Cl OCH₂CO₂ H H H  16 F Cl OCH₂CO₂ CH₃ H H  17 F Cl OCH₂CO₂ C₂H₅ H H  18 F Cl OCH₂CO₂ C₃H₇ H H  19 F Cl OCH₂CO₂ H CH₃ CH₃  20 F Cl OCH₂CO₂ CH₃ Ph CH₃  21 F Cl OCH₂CO₂ C₂H₅ Ph-4-Cl H  22 F Cl OCH₂CO₂ H H SCH₃  23 F Cl OCH₂CO₂ CN H H  24 F Cl OCH₂CO₂ Ph H H  25 F Cl OCH₂CO₂ CH₂Ph H H  26 F Cl OCH₂CO₂ Ph-4-Cl H H  27 F Cl OCH₂CO₂ CH₂Ph-4-Cl H H  28 F Cl OCH₂CO₂ 3-Py H H  29 F Cl OCH(CH₃)CO₂ H H H  30 F Cl OCH(CH₃)CO₂ CH₃ H H  31 F Cl OCH(CH₃)CO₂ C₂H₅ H H  32 F Cl OCH(CH₃)CO₂ C₃H₇ H H  33 F Cl OCH(CH₃)CO₂ H CH₃ CH₃  34 F Cl OCH(CH₃)CO₂ CH₃ Ph CH₃  35 F Cl CH═C(Cl)CO₂ H H H  36 F Cl CH₂CH(Cl)CO₂ H H H  37 F Cl OCH(CH₃)CO₂ CN H H  38 F Cl OCH(CH₃)CO₂ Ph H H  39 F Cl OCH(CH₃)CO₂ CH₂Ph H H  40 F Cl OCH(CH₃)CO₂ Ph-4-Cl H H  41 F Cl OCH(CH₃)CO₂ CH₂Ph-4-Cl H H  42 F Cl OCH(CH₃)CO₂ 3-Py H H  43 F Cl O H H H  44 F Cl O CH₃ H H  45 F Cl O C₂H₅ H H  46 F Cl O C₃H₇ H H  47 F Cl O H CH₃ CH₃  48 F Cl O CH₃ Ph CH₃  49 F Cl O C₂H₅ Ph-4-Cl H  50 F Cl O H H SCH₃  51 F Cl O CN H H  52 F Cl O Ph H H  53 F Cl O CH₂Ph H H  54 F Cl O Ph-4-Cl H H  55 F Cl O CH₂Ph-4-Cl H H  56 F Cl O 3-Py H H  57 F Cl SCH₂CO₂ H H H  58 F Cl SCH₂CO₂ CH₃ H H  59 F Cl SCH₂CO₂ C₂H₅ H H  60 F Cl SCH₂CO₂ C₃H₇ H H  61 F Cl SCH₂CO₂ H CH₃ CH₃  62 F Cl SCH₂CO₂ CH₃ Ph CH₃  63 F Cl SCH₂CO₂ C₂H₅ Ph-4-Cl H  64 F Cl SCH₂CO₂ H H SCH₃  65 F Cl SCH₂CO₂ CN H H  66 F Cl SCH₂CO₂ Ph H H  67 F Cl SCH₂CO₂ CH₂Ph H H  68 F Cl SCH₂CO₂ Ph-4-Cl H H  69 F Cl SCH₂CO₂ CH₂Ph-4-Cl H H  70 F Cl SCH₂CO₂ 3-Py H H  71 F H SCH(CH₃)CO₂ H H H  72 F Cl SCH(CH₃)CO₂ CH₃ H H  73 F Cl SCH(CH₃)CO₂ C₂H₅ H H  74 F Cl SCH(CH₃)CO₂ C₃H₇ H H  75 F Cl SCH(CH₃)CO₂ H CH₃ CH₃  76 F Cl SCH(CH₃)CO₂ CH₃ Ph CH₃  77 F Cl SCH(CH₃)CO₂ C₂H₅ Ph-4-Cl H  78 F Cl SCH(CH₃)CO₂ H H SCH₃  79 F Cl SCH(CH₃)CO₂ CN H H  80 F Cl SCH(CH₃)CO₂ Ph H H  81 F Cl SCH(CH₃)CO₂ CH₂Ph H H  82 F Cl SCH(CH₃)CO₂ Ph-4-Cl H H  83 F Cl SCH(CH₃)CO₂ CH₂Ph-4-Cl H H  84 F Cl SCH(CH₃)CO₂ 3-Py H H  85 F Cl S H H H  86 F Cl S CH₃ H H  87 F Cl S C₂H₅ H H  88 F Cl S C₃H₇ H H  89 F Cl S H CH₃ CH₃  90 F Cl S CH₃ Ph CH₃  91 F Cl S C₂H₅ Ph-4-Cl H  92 F Cl S H H SCH₃  93 F Cl S CN H H  94 F Cl S Ph H H  95 F Cl S CH₂Ph H H  96 F Cl S Ph-4-Cl H H  97 F Cl S CH₂Ph-4-Cl H H  98 F Cl S 3-Py H H  99 F Cl CH═C(Cl)CO₂ CN H H 100 F Cl CH₂CH(Cl)CO₂ CN H H 101 F Cl CH═C(Cl)CO₂ CH₃ H H 102 F Cl CH₂CH(Cl)CO₂ CH₃ H H 103 Cl Cl O H H H 104 Cl Cl OCH₂CO₂ H H H 105 Cl Cl OCH(CH₃)CO₂ H H H 106 Cl Cl CH═C(Cl)CO₂ H H H 107 Cl Cl CH₂CH(Cl)CO₂ H H H 108 Cl Cl CH₂CH(Cl)CO₂ CH₃ H H 109 Cl Cl SCH₂CO₂ H H H 110 Cl Cl SCH(CH₃)CO₂ H H H 111 Cl Cl CO₂ H H H 112 H Cl O H H H 113 H Cl OCH₂CO₂ H H H 114 H Cl OCH(CH₃)CO₂ H H H 115 H Cl CH═C(Cl)CO₂ H H H 116 H Cl CH₂CH(Cl)CO₂ H H H 117 H Cl S H H H 118 H Cl SCH₂CO₂ H H H 119 H Cl SCH(CH₃)CO₂ H H H 120 H Cl CH═C(Cl)CO₂ H H H 121 H Cl CH₂CH(Cl)CO₂ H H H 122 H Cl CO₂ H H H 123 F Cl OCH₂CONH H H H 124 F Cl SCH₂CONH H H H

TABLE 2

where A = N, B = CR₁₀ and Q = Q1 in a compound of formula I No R₁ R₂ X R₃ R₄ R₅ R₁₀ 125 F Cl CO₂ H H H H 126 F Cl CO₂ CH₃ H H H 127 F Cl CO₂ C₂H₅ H H H 128 F Cl CO₂ H Cl Cl CO₂CH₃ 129 F Cl CO₂ H CH₃ CH₃ H 130 F Cl CO₂ CH₃ Ph CH₃ H 131 F Cl CO₂ C₂H₅ Ph-4-Cl H H 132 F Cl CO₂ H C₂H₅ CO₂Et H 133 F Cl CO₂ CN H H H 134 F Cl CO₂ Ph H H H 135 F Cl CO₂ CH₂Ph H H H 136 F Cl CO₂ Ph-4-Cl H H H 137 F Cl CO₂ CH₂Ph-4-Cl H H H 138 F Cl CO₂ 3-Py H H H 139 F Cl OCH₂CO₂ H H H H 140 F Cl OCH₂CO₂ CH₃ H H H 141 F Cl OCH₂CO₂ C₂H₅ H H H 142 F Cl OCH₂CO₂ H Cl Cl CO₂CH₃ 143 F Cl OCH₂CO₂ H CH₃ CH₃ H 144 F Cl OCH₂CO₂ CH₃ Ph CH₃ H 145 F Cl OCH₂CO₂ C₂H₅ Ph-4-Cl H H 146 F Cl OCH₂CO₂ H C₂H₅ CO₂Et H 147 F Cl OCH₂CO₂ CN H H H 148 F Cl OCH₂CO₂ Ph H H H 149 F Cl OCH₂CO₂ CH₂Ph H H H 150 F Cl OCH₂CO₂ Ph-4-Cl H H H 151 F Cl OCH₂CO₂ CH₂Ph-4-Cl H H H 152 F Cl OCH₂CO₂ 3-Py H H H 153 F Cl OCH(CH₃)CO₂ H H H H 154 F Cl OCH(CH₃)CO₂ CH₃ H H H 155 F Cl OCH(CH₃)CO₂ C₂H₅ H H H 156 F Cl OCH(CH₃)CO₂ H Cl Cl CO₂CH₃ 157 F Cl OCH(CH₃)CO₂ H CH₃ CH₃ H 158 F Cl OCH(CH₃)CO₂ CH₃ Ph CH₃ H 159 F Cl OCH(CH₃)CO₂ C₂H₅ Ph-4-Cl H H 160 F Cl OCH(CH₃)CO₂ H C₂H₅ CO₂Et H 161 F Cl OCH(CH₃)CO₂ CN H H H 162 F Cl OCH(CH₃)CO₂ Ph H H H 163 F Cl OCH(CH₃)CO₂ CH₂Ph H H H 164 F Cl OCH(CH₃)CO₂ Ph-4-Cl H H H 165 F Cl OCH(CH₃)CO₂ CH₂Ph-4-Cl H H H 166 F Cl OCH(CH₃)CO₂ 3-Py H H H 167 F Cl O H H H H 168 F Cl O CH₃ H H H 169 F Cl O C₂H₅ H H H 170 F Cl O H Cl Cl CO₂CH₃ 171 F Cl O H CH₃ CH₃ H 172 F Cl O CH₃ Ph CH₃ H 173 F Cl O C₂H₅ Ph-4-Cl H H 174 F Cl O H C₂H₅ CO₂Et H 175 F Cl O CN H H H 176 F Cl O Ph H H H 177 F Cl O CH₂Ph H H H 178 F Cl O Ph-4-Cl H H H 179 F Cl O CH₂Ph-4-Cl H H H 180 F Cl O 3-Py H H H 181 F Cl SCH₂CO₂ H H H H 182 F Cl SCH₂CO₂ CH₃ H H H 183 F Cl SCH₂CO₂ C₂H₅ H H H 184 F Cl SCH₂CO₂ H Cl Cl CO₂CH₃ 185 F Cl SCH₂CO₂ H CH₃ CH₃ H 186 F Cl SCH₂CO₂ CH₃ Ph CH₃ H 187 F Cl SCH₂CO₂ C₂H₅ Ph-4-Cl H H 188 F Cl SCH₂CO₂ H C₂H₅ CO₂Et H 189 F Cl SCH₂CO₂ CN H H H 190 F Cl SCH₂CO₂ Ph H H H 191 F Cl SCH₂CO₂ CH₂Ph H H H 192 F Cl SCH₂CO₂ Ph-4-Cl H H H 193 F Cl SCH₂CO₂ CH₂Ph-4-Cl H H H 194 F Cl SCH₂CO₂ 3-Py H H H 195 F Cl SCH(CH₃)CO₂ H H H H 196 F Cl SCH(CH₃)CO₂ CH₃ H H H 197 F Cl SCH(CH₃)CO₂ C₂H₅ H H H 198 F Cl SCH(CH₃)CO₂ H Cl Cl CO₂CH₃ 199 F Cl SCH(CH₃)CO₂ H CH₃ CH₃ H 200 F Cl SCH(CH₃)CO₂ CH₃ Ph CH₃ H 201 F Cl SCH(CH₃)CO₂ C₂H₅ Ph-4-Cl H H 202 F Cl SCH(CH₃)CO₂ H C₂H₅ CO₂Et H 203 F Cl SCH(CH₃)CO₂ CN H H H 204 F Cl SCH(CH₃)CO₂ Ph H H H 205 F Cl SCH(CH₃)CO₂ CH₂Ph H H H 206 F Cl SCH(CH₃)CO₂ Ph-4-Cl H H H 207 F Cl SCH(CH₃)CO₂ CH₂Ph-4-Cl H H H 208 F Cl SCH(CH₃)CO₂ 3-Py H H H 209 F Cl S H H H H 210 F Cl S CH₃ H H H 211 F Cl S C₂H₅ H H H 212 F Cl S H Cl Cl CO₂CH₃ 213 F Cl S H CH₃ CH₃ H 214 F Cl S CH₃ Ph CH₃ H 215 F Cl S C₂H₅ Ph-4-Cl H H 216 F Cl S H C₂H₅ CO₂Et H 217 F Cl S CN H H H 218 F Cl S Ph H H H 219 F Cl S CH₂Ph H H H 220 F Cl S Ph-4-Cl H H H 221 F Cl S CH₂Ph-4-Cl H H H 222 F Cl S 3-Py H H H 223 F Cl CH═C(Cl)CO₂ H H H H 224 F Cl CH₂CH(Cl)CO₂ H H H H 225 Cl Cl O H H H H 226 Cl Cl OCH₂CO₂ H H H H 227 Cl Cl S H H H H 228 Cl Cl SCH₂CO₂ H H H H 229 Cl Cl SCH(CH₃)CO₂ H H H H 230 Cl Cl CO₂ H H H H 231 H Cl O H H H H 232 H Cl OCH₂CO₂ H H H H 233 H Cl S H H H H 234 H Cl SCH₂CO₂ H H H H 235 H Cl CO₂ H H H H

TABLE 3

where A = CH, B = N and Q = Q1 in a compound of formula I No R₁ R₂ X R₃ R₄ R₅ 236 F Cl CO₂ H H H 237 F Cl CO₂ CH₃ H H 238 F Cl CO₂ C₂H₅ H H 239 F Cl CO₂ H Cl Cl 240 F Cl CO₂ H CH₃ CH₃ 241 F Cl CO₂ CH₃ Ph CH₃ 242 F Cl CO₂ C₂H₅ Ph-4-Cl H 243 F Cl CO₂ H Ph-4-Cl CH₃ 244 F Cl CO₂ CN H H 245 F Cl CO₂ Ph H H 246 F Cl CO₂ CH₂Ph H H 247 F Cl CO₂ Ph-4-Cl H H 248 F Cl CO₂ CH₂Ph-4-Cl H H 249 F Cl CO₂ 3-Py H H 250 F Cl OCH₂CO₂ H H H 251 F Cl OCH₂CO₂ CH₃ H H 252 F Cl OCH₂CO₂ C₂H₅ H H 253 F Cl OCH₂CO₂ H Cl Cl 254 F Cl OCH₂CO₂ H CH₃ CH₃ 255 F Cl OCH₂CO₂ CH₃ Ph CH₃ 256 F Cl OCH₂CO₂ C₂H₅ Ph-4-Cl H 257 F Cl OCH₂CO₂ H Ph-4-Cl CH₃ 258 F Cl OCH₂CO₂ CN H H 259 F Cl OCH₂CO₂ Ph H H 260 F Cl OCH₂CO₂ CH₂Ph H H 261 F Cl OCH₂CO₂ Ph-4-Cl H H 262 F Cl OCH₂CO₂ CH₂Ph-4-Cl H H 263 F Cl OCH₂CO₂ 3-Py H H 264 F Cl OCH(CH₃)CO₂ H H H 265 F Cl OCH(CH₃)CO₂ CH₃ H H 266 F Cl OCH(CH₃)CO₂ C₂H₅ H H 267 F Cl OCH(CH₃)CO₂ H Cl Cl 268 F Cl OCH(CH₃)CO₂ H CH₃ CH₃ 269 F Cl OCH(CH₃)CO₂ CH₃ Ph CH₃ 270 F Cl OCH(CH₃)CO₂ C₂H₅ Ph-4-Cl H 271 F Cl OCH(CH₃)CO₂ H Ph-4-Cl CH₃ 272 F Cl OCH(CH₃)CO₂ CN H H 273 F Cl OCH(CH₃)CO₂ Ph H H 274 F Cl OCH(CH₃)CO₂ CH₂Ph H H 275 F Cl OCH(CH₃)CO₂ Ph-4-Cl H H 276 F Cl OCH(CH₃)CO₂ CH₂Ph-4-Cl H H 277 F Cl OCH(CH₃)CO₂ 3-Py H H 278 F Cl O H H H 279 F Cl O CH₃ H H 280 F Cl O C₂H₅ H H 281 F Cl O H Cl Cl 282 F Cl O H CH₃ CH₃ 283 F Cl O CH₃ Ph CH₃ 284 F Cl O C₂H₅ Ph-4-Cl H 285 F Cl O H Ph-4-Cl CH₃ 286 F Cl O CN H H 287 F Cl O Ph H H 288 F Cl O CH₂Ph H H 289 F Cl O Ph-4-Cl H H 290 F Cl O CH₂Ph-4-Cl H H 291 F Cl O 3-Py H H 292 F Cl SCH₂CO₂ H H H 293 F Cl SCH₂CO₂ CH₃ H H 294 F Cl SCH₂CO₂ C₂H₅ H H 295 F Cl SCH₂CO₂ H Cl Cl 296 F Cl SCH₂CO₂ H CH₃ CH₃ 297 F Cl SCH₂CO₂ CH₃ Ph CH₃ 298 F Cl SCH₂CO₂ C₂H₅ Ph-4-Cl H 299 F Cl SCH₂CO₂ H Ph-4-Cl CH₃ 300 F Cl SCH₂CO₂ CN H H 301 F Cl SCH₂CO₂ Ph H H 302 F Cl SCH₂CO₂ CH₂Ph H H 303 F Cl SCH₂CO₂ Ph-4-Cl H H 304 F Cl SCH₂CO₂ CH₂Ph-4-Cl H H 305 F Cl SCH₂CO₂ 3-Py H H 306 F Cl SCH(CH₃)CO₂ H H H 307 F Cl SCH(CH₃)CO₂ CH₃ H H 308 F Cl SCH(CH₃)CO₂ C₂H₅ H H 309 F Cl SCH(CH₃)CO₂ H Cl Cl 310 F Cl SCH(CH₃)CO₂ H CH₃ CH₃ 311 F Cl SCH(CH₃)CO₂ CH₃ Ph CH₃ 312 F Cl SCH(CH₃)CO₂ C₂H₅ Ph-4-Cl H 313 F Cl SCH(CH₃)CO₂ H Ph-4-Cl CH₃ 314 F Cl SCH(CH₃)CO₂ CN H H 315 F Cl SCH(CH₃)CO₂ Ph H H 316 F Cl S H H H 317 F Cl S CH₃ H H 318 F Cl S C₂H₅ H H 319 F Cl S H Cl Cl 320 F Cl S H CH₃ CH₃ 321 F Cl S CH₃ Ph CH₃ 322 F Cl S C₂H₅ Ph-4-Cl H 323 F Cl CH═C(Cl)CO₂ H H H 324 F Cl CH₂CH(Cl)CO₂ H H H 325 F Cl S Ph H H 326 F Cl S CH₂Ph CH₃ CH₃ 327 F Cl S Ph-4-Cl H H 328 Cl Cl O H H H 329 Cl Cl OCH₂CO₂ H H H 330 Cl Cl S H H H 331 Cl Cl SCH₂CO₂ H H H 332 Cl Cl SCH(CH₃)CO₂ H H H 333 Cl Cl CO₂ H H H 334 H Cl O H H H 335 H Cl OCH₂CO₂ H H H 336 H Cl S H H H 337 H Cl SCH₂CO₂ H H H 338 H Cl CO₂ H H H

TABLE 4

where A = B = N, R₄ = R₅ = H and Q = Q2 in a compound of formula I No R₁ R₂ X R₃ 339 F Cl CO₂ H 340 F Cl CO₂ CH₃ 341 F Cl CO₂ C₂H₅ 342 F Cl CO₂ Ph 343 F Cl CO₂ CH₂Ph 344 F Cl CO₂ Ph-4-Cl 345 F Cl CO₂ CN 346 F Cl CO₂ 3-Py 347 F Cl OCH₂CO₂ H 348 F Cl OCH₂CO₂ CH₃ 349 F Cl OCH₂CO₂ C₂H₅ 350 F Cl OCH₂CO₂ Ph 351 F Cl OCH₂CO₂ CH₂Ph 352 F Cl OCH₂CO₂ Ph-4-Cl 353 F Cl OCH₂CO₂ CN 354 F Cl OCH₂CO₂ 3-Py 355 F Cl OCH(CH₃)CO₂ H 356 F Cl OCH(CH₃)CO₂ CH₃ 357 F Cl OCH(CH₃)CO₂ C₂H₅ 358 F Cl OCH(CH₃)CO₂ Ph 359 F Cl OCH(CH₃)CO₂ CH₂Ph 360 F Cl OCH(CH₃)CO₂ Ph-4-Cl 361 F Cl CH═C(Cl)CO₂ H 362 F Cl CH₂CH(Cl)CO₂ H 363 F Cl O H 364 F Cl O CH₃ 365 F Cl O C₂H₅ 366 F Cl O Ph 367 F Cl O CH₂Ph 368 F Cl CH═C(Cl)CO₂ CN 369 F Cl CH₂CH(Cl)CO₂ CN 370 F Cl O 3-Py 371 F Cl SCH₂CO₂ H 372 F Cl SCH₂CO₂ CH₃ 373 F Cl SCH₂CO₂ C₂H₅ 374 F Cl SCH₂CO₂ Ph 375 F Cl SCH₂CO₂ CH₂Ph 376 F Cl SCH₂CO₂ Ph-4-Cl 377 F Cl SCH₂CO₂ CN 378 F Cl SCH₂CO₂ 3-Py 379 F H SCH(CH₃)CO₂ H 380 F Cl SCH(CH₃)CO₂ CH₃ 381 F Cl SCH(CH₃)CO₂ C₂H₅ 382 F Cl SCH(CH₃)CO₂ Ph 383 F Cl SCH(CH₃)CO₂ CH₂Ph 384 F Cl SCH(CH₃)CO₂ Ph-4-Cl 385 F Cl SCH(CH₃)CO₂ CH₂Ph-4-Cl 386 F Cl SCH(CH₃)CO₂ 3-Py 387 F Cl S H 388 F Cl S CH₃ 389 F Cl S C₂H₅ 390 F Cl S Ph 391 F Cl S CH₂Ph 392 F Cl S Ph-4-Cl 393 F Cl S CH₂Ph-4-Cl 394 F Cl S 3-Py 395 Cl Cl O H 396 Cl Cl OCH₂CO₂ H 397 Cl Cl OCH(CH₃)CO₂ H 398 Cl Cl CH═C(Cl)CO₂ H 399 Cl Cl CH₂CH(Cl)CO₂ H 400 Cl Cl S H 401 Cl Cl SCH₂CO₂ H 402 Cl Cl SCH(CH₃)CO₂ H 403 Cl Cl CO₂ H 404 H Cl O H 405 H Cl OCH₂CO₂ H 406 H Cl OCH(CH₃)CO₂ H 407 H Cl CH═C(Cl)CO₂ H 408 H Cl CH₂CH(Cl)CO₂ H 409 H Cl S H 410 H Cl SCH₂CO₂ H 411 H Cl SCH(CH₃)CO₂ H 412 H Cl CH═C(Cl)CO₂ H 413 H Cl CH₂CH(Cl)CO₂ H 414 H Cl CO₂ H 415 F Cl OCH₂CO₂ Ph-4-F 416 F Cl SCH₂CO₂ Ph-4-F

TABLE 5

where A = N, B = CH, R₄ = R₅ = CH₃, Q = Q2 in a compound of formula I No R₁ R₂ X R₃ 417 F Cl CO₂ H 418 F Cl CO₂ CH₃ 419 F Cl CO₂ C₂H₅ 420 F Cl CO₂ Ph 421 F Cl CO₂ CH₂Ph 422 F Cl CO₂ Ph-4-Cl 423 F Cl CO₂ CN 424 F Cl CO₂ 3-Py 425 F Cl OCH₂CO₂ H 426 F Cl OCH₂CO₂ CH₃ 427 F Cl OCH₂CO₂ C₂H₅ 428 F Cl OCH₂CO₂ Ph 429 F Cl OCH₂CO₂ CH₂Ph 430 F Cl OCH₂CO₂ Ph-4-Cl 431 F Cl OCH₂CO₂ CH₂Ph-4-Cl 432 F Cl OCH₂CO₂ 3-Py 433 F Cl OCH(CH₃)CO₂ H 434 F Cl OCH(CH₃)CO₂ CH₃ 435 F Cl OCH(CH₃)CO₂ C₂H₅ 436 F Cl OCH(CH₃)CO₂ Ph 437 F Cl OCH(CH₃)CO₂ CH₂Ph 438 F Cl OCH(CH₃)CO₂ Ph-4-Cl 439 F Cl OCH(CH₃)CO₂ CN 440 F Cl OCH(CH₃)CO₂ 3-Py 441 F Cl O H 442 F Cl O CH₃ 443 F Cl O C₂H₅ 444 F Cl O Ph 445 F Cl O CH₂Ph 446 F Cl O Ph-4-Cl 447 F Cl O CH₂Ph-4-Cl 448 F Cl O 3-Py 449 F Cl SCH₂CO₂ H 450 F Cl SCH₂CO₂ CH₃ 451 F Cl SCH₂CO₂ C₂H₅ 452 F Cl SCH₂CO₂ Ph 453 F Cl SCH₂CO₂ CH₂Ph 454 F Cl SCH₂CO₂ Ph-4-Cl 455 F Cl SCH₂CO₂ CH₂Ph-4-Cl 456 F Cl SCH₂CO₂ 3-Py 457 F Cl SCH(CH₃)CO₂ H 458 F Cl SCH(CH₃)CO₂ CH₃ 459 F Cl SCH(CH₃)CO₂ C₂H₅ 460 F Cl SCH(CH₃)CO₂ Ph 461 F Cl SCH(CH₃)CO₂ CH₂Ph 462 F Cl SCH(CH₃)CO₂ Ph-4-Cl 463 F Cl SCH(CH₃)CO₂ CH₂Ph-4-Cl 464 F Cl SCH(CH₃)CO₂ 3-Py 465 F Cl S H 466 F Cl S CH₃ 467 F Cl S C₂H₅ 468 F Cl S Ph 469 F Cl S CH₂Ph 470 F Cl S Ph-4-Cl 471 F Cl S CH₂Ph-4-Cl 472 F Cl S 3-Py 473 Cl Cl O H 474 Cl Cl OCH₂CO₂ H 475 Cl Cl S H 476 Cl Cl SCH₂CO₂ H 477 Cl Cl SCH(CH₃)CO₂ H 478 Cl Cl CO₂ H 479 H Cl O H 480 H Cl OCH₂CO₂ H 481 H Cl S H 482 H Cl SCH₂CO₂ H 483 H Cl CO₂ H

TABLE 6

where A = CH, B = N, R₄ = R₅ = H, Q = Q2 in a compound of formula I No R₁ R₂ X R₃ 484 F Cl CO₂ H 485 F Cl CO₂ CH₃ 486 F Cl CO₂ C₂H₅ 487 F Cl CO₂ Ph 488 F Cl CO₂ CH₂Ph 489 F Cl CO₂ Ph-4-Cl 490 F Cl CO₂ CH₂Ph-4-Cl 491 F Cl CO₂ 3-Py 492 F Cl OCH₂CO₂ H 493 F Cl OCH₂CO₂ CH₃ 494 F Cl OCH₂CO₂ C₂H₅ 495 F Cl OCH₂CO₂ Ph 496 F Cl OCH₂CO₂ CH₂Ph 497 F Cl OCH₂CO₂ CN 498 F Cl OCH₂CO₂ CH₂Ph-4-Cl 499 F Cl OCH₂CO₂ 3-Py 500 F Cl OCH(CH₃)CO₂ H 501 F Cl OCH(CH₃)CO₂ CH₃ 502 F Cl OCH(CH₃)CO₂ C₂H₅ 503 F Cl OCH(CH₃)CO₂ Ph 504 F Cl OCH(CH₃)CO₂ CH₂Ph 505 F Cl OCH(CH₃)CO₂ Ph-4-Cl 506 F Cl OCH(CH₃)CO₂ CH₂Ph-4-Cl 507 F Cl OCH(CH₃)CO₂ 3-Py 508 F Cl O H 509 F Cl O CH₃ 510 F Cl O C₂H₅ 511 F Cl O Ph 512 F Cl O CH₂Ph 513 F Cl O Ph-4-Cl 514 F Cl O CH₂Ph-4-Cl 515 F Cl O 3-Py 516 F Cl SCH₂CO₂ H 517 F Cl SCH₂CO₂ CH₃ 518 F Cl SCH₂CO₂ C₂H₅ 519 F Cl SCH₂CO₂ Ph 520 F Cl SCH₂CO₂ CH₂Ph 521 F Cl SCH₂CO₂ Ph-4-Cl 522 F Cl SCH₂CO₂ CH₂Ph-4-Cl 523 F Cl SCH₂CO₂ 3-Py 524 F Cl SCH(CH₃)CO₂ H 525 F Cl SCH(CH₃)CO₂ CH₃ 526 F Cl SCH(CH₃)CO₂ C₂H₅ 527 F Cl SCH(CH₃)CO₂ Ph 528 F Cl SCH(CH₃)CO₂ CH₂Ph 529 F Cl SCH(CH₃)CO₂ Ph-4-Cl 530 F Cl SCH(CH₃)CO₂ CH₂Ph-4-Cl 531 F Cl SCH(CH₃)CO₂ 3-Py 532 F Cl S H 533 F Cl S CH₃ 534 F Cl S C₂H₅ 535 F Cl S Ph 536 F Cl S CH₂Ph 537 F Cl S Ph-4-Cl 538 F Cl S CH₂Ph-4-Cl 539 F Cl S 3-Py 540 Cl Cl O H 541 Cl Cl OCH₂CO₂ H 542 Cl Cl S H 543 Cl Cl SCH₂CO₂ H 544 Cl Cl SCH(CH₃)CO₂ H 545 Cl Cl CO₂ H 546 H Cl O H 547 H Cl OCH₂CO₂ H 548 H Cl S H 549 H Cl SCH₂CO₂ H 550 H Cl CO₂ H

TABLE 7

where A = B = N, R₄ = R₅ = H, Q = Q3 in a compound of formula I No R₁ R₂ X R₃ 551 F Cl CO₂ H 552 F Cl CO₂ CH₃ 553 F Cl CO₂ C₂H₅ 554 F Cl CO₂ Ph 555 F Cl CO₂ CH₂Ph 556 F Cl CO₂ Ph-4-Cl 557 F Cl CO₂ CN 558 F Cl CO₂ 3-Py 559 F Cl OCH₂CO₂ H 560 F Cl OCH₂CO₂ CH₃ 561 F Cl OCH₂CO₂ C₂H₅ 562 F Cl OCH₂CO₂ Ph 563 F Cl OCH₂CO₂ CH₂Ph 564 F Cl OCH₂CO₂ Ph-4-Cl 565 F Cl OCH₂CO₂ CN 566 F Cl OCH₂CO₂ 3-Py 567 F Cl OCH(CH₃)CO₂ H 568 F Cl OCH(CH₃)CO₂ CH₃ 569 F Cl OCH(CH₃)CO₂ C₂H₅ 570 F Cl OCH(CH₃)CO₂ Ph 571 F Cl OCH(CH₃)CO₂ CH₂Ph 572 F Cl OCH(CH₃)CO₂ Ph-4-Cl 573 F Cl OCH(CH₃)CO₂ CN 574 F Cl OCH(CH₃)CO₂ 3-Py 575 F Cl O H 576 F Cl O CH₃ 577 F Cl O C₂H₅ 578 F Cl O Ph 579 F Cl O CH₂Ph 580 F Cl O Ph-4-Cl 581 F Cl O CH₂Ph-4-Cl 582 F Cl O 3-Py 583 F Cl SCH₂CO₂ H 584 F Cl SCH₂CO₂ CH₃ 585 F Cl SCH₂CO₂ C₂H₅ 586 F Cl SCH₂CO₂ Ph 587 F Cl SCH₂CO₂ CH₂Ph 588 F Cl SCH₂CO₂ Ph-4-Cl 589 F Cl SCH₂CO₂ CH₂Ph-4-Cl 590 F Cl SCH₂CO₂ 3-Py 591 F H SCH(CH₃)CO₂ H 592 F Cl SCH(CH₃)CO₂ CH₃ 593 F Cl SCH(CH₃)CO₂ C₂H₅ 594 F Cl SCH(CH₃)CO₂ Ph 595 F Cl SCH(CH₃)CO₂ CH₂Ph 596 F Cl SCH(CH₃)CO₂ Ph-4-Cl 597 F Cl SCH(CH₃)CO₂ CH₂Ph-4-Cl 598 F Cl SCH(CH₃)CO₂ 3-Py 599 F Cl S H 600 F Cl S CH₃ 601 F Cl S C₂H₅ 602 F Cl S Ph 603 F Cl S CH₂Ph 604 F Cl S Ph-4-Cl 605 F Cl S CH₂Ph-4-Cl 606 F Cl S 3-Py 607 F Cl CH═C(Cl)CO₂ H 608 F Cl CH₂CH(Cl)CO₂ H 609 Cl Cl O H 610 Cl Cl OCH₂CO₂ H 611 Cl Cl CH═C(Cl)CO₂ H 612 Cl Cl CH₂CH(Cl)CO₂ H 613 Cl Cl SCH₂CO₂ H 614 Cl Cl SCH(CH₃)CO₂ H 615 Cl Cl CO₂ H 616 H Cl OCH₂CO₂ H 617 H Cl CH═C(Cl)CO₂ H 618 H Cl CH₂CH(Cl)CO₂ H 619 H Cl S H 620 H Cl SCH₂CO₂ H 621 H Cl SCH(CH₃)CO₂ H 622 H Cl CO₂ H 623 F Cl OCH₂CO₂ Ph-4-F 624 F Cl SCH₂CO₂ Ph-4-F

TABLE 8

where A = N, B = CH, R₄ = R₅ = CH₃, Q = Q3 in a compound of formula I No R₁ R₂ X R₃ 625 F Cl CO₂ H 626 F Cl CO₂ CH₃ 627 F Cl CO₂ C₂H₅ 628 F Cl CO₂ Ph 629 F Cl CO₂ CH₂Ph 630 F Cl CO₂ Ph-4-Cl 631 F Cl CO₂ CH₂Ph-4-Cl 632 F Cl CO₂ 3-Py 633 F Cl OCH₂CO₂ H 634 F Cl OCH₂CO₂ CH₃ 635 F Cl OCH₂CO₂ C₂H₅ 636 F Cl OCH₂CO₂ Ph 637 F Cl OCH₂CO₂ CH₂Ph 638 F Cl OCH₂CO₂ Ph-4-Cl 639 F Cl OCH₂CO₂ CH₂Ph-4-Cl 640 F Cl OCH₂CO₂ 3-Py 641 F Cl OCH(CH₃)CO₂ H 642 F Cl OCH(CH₃)CO₂ CH₃ 643 F Cl OCH(CH₃)CO₂ C₂H₅ 644 F Cl OCH(CH₃)CO₂ Ph 645 F Cl OCH(CH₃)CO₂ CH₂Ph 646 F Cl OCH(CH₃)CO₂ Ph-4-Cl 647 F Cl OCH(CH₃)CO₂ CH₂Ph-4-Cl 648 F Cl OCH(CH₃)CO₂ 3-Py 649 F Cl O H 650 F Cl O CH₃ 651 F Cl O C₂H₅ 652 F Cl O Ph 653 F Cl O CH₂Ph 654 F Cl O Ph-4-Cl 655 F Cl O CH₂Ph-4-Cl 656 F Cl O 3-Py 657 F Cl SCH₂CO₂ H 658 F Cl SCH₂CO₂ CH₃ 659 F Cl SCH₂CO₂ C₂H₅ 660 F Cl SCH₂CO₂ Ph 661 F Cl SCH₂CO₂ CH₂Ph 662 F Cl SCH₂CO₂ Ph-4-Cl 663 F Cl SCH₂CO₂ CH₂Ph-4-Cl 664 F Cl SCH₂CO₂ 3-Py 665 F Cl SCH(CH₃)CO₂ H 666 F Cl SCH(CH₃)CO₂ CH₃ 667 F Cl SCH(CH₃)CO₂ C₂H₅ 668 F Cl SCH(CH₃)CO₂ Ph 669 F Cl SCH(CH₃)CO₂ CH₂Ph 670 F Cl SCH(CH₃)CO₂ Ph-4-Cl 671 F Cl SCH(CH₃)CO₂ CH₂Ph-4-Cl 672 F Cl SCH(CH₃)CO₂ 3-Py 673 F Cl S H 674 F Cl S CH₃ 675 F Cl S C₂H₅ 676 F Cl S Ph 677 F Cl S CH₂Ph 678 F Cl S Ph-4-Cl 679 F Cl S CH₂Ph-4-Cl 680 F Cl S 3-Py

TABLE 9

where A = CH, B = N, R₄ = R₅ = H, Q = Q3 in a compound of formula I No R₁ R₂ X R₃ 681 F Cl CO₂ H 682 F Cl CO₂ CH₃ 683 F Cl CO₂ C₂H₅ 684 F Cl CO₂ Ph 685 F Cl CO₂ CH₂Ph 686 F Cl CO₂ Ph-4-Cl 687 F Cl CO₂ CH₂Ph-4-Cl 688 F Cl CO₂ 3-Py 689 F Cl OCH₂CO₂ H 690 F Cl OCH₂CO₂ CH₃ 691 F Cl OCH₂CO₂ C₂H₅ 692 F Cl OCH₂CO₂ Ph 693 F Cl OCH₂CO₂ CH₂Ph 694 F Cl OCH₂CO₂ Ph-4-Cl 695 F Cl OCH₂CO₂ CH₂Ph-4-Cl 696 F Cl OCH₂CO₂ 3-Py 697 F Cl OCH(CH₃)CO₂ H 698 F Cl OCH(CH₃)CO₂ CH₃ 699 F Cl OCH(CH₃)CO₂ C₂H₅ 700 F Cl OCH(CH₃)CO₂ Ph 701 F Cl OCH(CH₃)CO₂ CH₂Ph 702 F Cl OCH(CH₃)CO₂ Ph-4-Cl 703 F Cl OCH(CH₃)CO₂ CH₂Ph-4-Cl 704 F Cl OCH(CH₃)CO₂ 3-Py 705 F Cl O H 706 F Cl O CH₃ 707 F Cl O C₂H₅ 708 F Cl O Ph 709 F Cl O CH₂Ph 710 F Cl O Ph-4-Cl 711 F Cl O CH₂Ph-4-Cl 712 F Cl O 3-Py 713 F Cl SCH₂CO₂ H 714 F Cl SCH₂CO₂ CH₃ 715 F Cl SCH₂CO₂ C₂H₅ 716 F Cl SCH₂CO₂ Ph 717 F Cl SCH₂CO₂ CH₂Ph 718 F Cl SCH₂CO₂ Ph-4-Cl 719 F Cl SCH₂CO₂ CH₂Ph-4-Cl 720 F Cl SCH₂CO₂ 3-Py 721 F Cl SCH(CH₃)CO₂ H 722 F Cl SCH(CH₃)CO₂ CH₃ 723 F Cl SCH(CH₃)CO₂ C₂H₅ 724 F Cl SCH(CH₃)CO₂ Ph 725 F Cl SCH(CH₃)CO₂ CH₂Ph 726 F Cl SCH(CH₃)CO₂ Ph-4-Cl 727 F Cl S H 728 F Cl S CH₃ 729 F Cl S C₂H₅ 730 F Cl S Ph 731 F Cl S CH₂Ph 732 F Cl S Ph-4-Cl 733 F Cl S CH₂Ph-4-Cl 734 F Cl S 3-Py

TABLE 10

where A = B = N, R₄ = R₅ = H, Q = Q4 in a compound of formula I No R₁ R₂ X R₃ 735 F Cl CO₂ H 736 F Cl CO₂ CH₃ 737 F Cl CO₂ C₂H₅ 738 F Cl CO₂ Ph 739 F Cl CO₂ CH₂Ph 740 F Cl CO₂ Ph-4-Cl 741 F Cl CO₂ CN 742 F Cl CO₂ 3-Py 743 F Cl OCH₂CO₂ H 744 F Cl OCH₂CO₂ CH₃ 745 F Cl OCH₂CO₂ C₂H₅ 746 F Cl OCH₂CO₂ Ph 747 F Cl OCH₂CO₂ CH₂Ph 748 F Cl OCH₂CO₂ Ph-4-Cl 749 F Cl OCH₂CO₂ CN 750 F Cl OCH₂CO₂ 3-Py 751 F Cl OCH(CH₃)CO₂ H 752 F Cl OCH(CH₃)CO₂ CH₃ 753 F Cl OCH(CH₃)CO₂ C₂H₅ 754 F Cl OCH(CH₃)CO₂ Ph 755 F Cl OCH(CH₃)CO₂ CH₂Ph 756 F Cl OCH(CH₃)CO₂ Ph-4-Cl 757 F Cl OCH(CH₃)CO₂ CN 758 F Cl OCH(CH₃)CO₂ 3-Py 759 F Cl O H 760 F Cl O CH₃ 761 F Cl O C₂H₅ 762 F Cl O Ph 763 F Cl O CH₂Ph 764 F Cl O Ph-4-Cl 765 F Cl O CN 766 F Cl O 3-Py 767 F Cl SCH₂CO₂ H 768 F Cl SCH₂CO₂ CH₃ 769 F Cl SCH₂CO₂ C₂H₅ 770 F Cl SCH₂CO₂ Ph 771 F Cl SCH₂CO₂ CH₂Ph 772 F Cl SCH₂CO₂ Ph-4-Cl 773 F Cl SCH₂CO₂ CN 774 F Cl SCH₂CO₂ 3-Py 775 F H SCH(CH₃)CO₂ H 776 F Cl SCH(CH₃)CO₂ CH₃ 777 F Cl SCH(CH₃)CO₂ C₂H₅ 778 F Cl SCH(CH₃)CO₂ Ph 779 F Cl SCH(CH₃)CO₂ CH₂Ph 780 F Cl SCH(CH₃)CO₂ Ph-4-Cl 781 F Cl SCH(CH₃)CO₂ CH₂Ph-4-Cl 782 F Cl SCH(CH₃)CO₂ 3-Py 783 F Cl S H 784 F Cl S CH₃ 785 F Cl S C₂H₅ 786 F Cl S Ph 787 F Cl CH═C(Cl)CO₂ CN 788 F Cl CH₂CH(Cl)CO₂ CN 789 F Cl CH═C(Cl)CO₂ H 790 F Cl CH₂CH(Cl)CO₂ H 791 Cl Cl O H 792 Cl Cl OCH₂CO₂ H 793 Cl Cl OCH(CH₃)CO₂ H 794 Cl Cl SCH₂CO₂ H 795 Cl Cl CH═C(Cl)CO₂ H 796 Cl Cl CH₂CH(Cl)CO₂ H 797 Cl Cl CO₂ H 798 H Cl O H 799 H Cl OCH₂CO₂ H 800 H Cl OCH(CH₃)CO₂ H 801 H Cl SCH₂CO₂ H 802 H Cl CH═C(Cl)CO₂ H 803 H Cl CH₂CH(Cl)CO₂ H 804 H Cl CO₂ H 805 F Cl OCH₂CO₂ Ph-4-F 806 F Cl SCH₂CO₂ Ph-4-F

TABLE 11

where A = B = N, R₄ = R₅ = H, Q = Q5 in a compound of formula I No R₁ R₂ X R₃ 807 F Cl CO₂ H 808 F Cl CO₂ CH₃ 809 F Cl CO₂ C₂H₅ 810 F Cl CO₂ Ph 811 F Cl CO₂ CH₂Ph 812 F Cl CO₂ Ph-4-Cl 813 F Cl CO₂ CN 814 F Cl CO₂ 3-Py 815 F Cl OCH₂CO₂ H 816 F Cl OCH₂CO₂ CH₃ 817 F Cl OCH₂CO₂ C₂H₅ 818 F Cl OCH₂CO₂ Ph 819 F Cl OCH₂CO₂ CH₂Ph 820 F Cl OCH₂CO₂ Ph-4-Cl 821 F Cl OCH₂CO₂ CN 822 F Cl OCH₂CO₂ 3-Py 823 F Cl OCH(CH₃)CO₂ H 824 F Cl OCH(CH₃)CO₂ CH₃ 825 F Cl OCH(CH₃)CO₂ C₂H₅ 826 F Cl OCH(CH₃)CO₂ Ph 827 F Cl OCH(CH₃)CO₂ CH₂Ph 828 F Cl OCH(CH₃)CO₂ Ph-4-Cl 829 F Cl OCH(CH₃)CO₂ CN 830 F Cl OCH(CH₃)CO₂ 3-Py 831 F Cl O H 832 F Cl O CH₃ 833 F Cl O C₂H₅ 834 F Cl O Ph 835 F Cl O CH₂Ph 836 F Cl O Ph-4-Cl 837 F Cl O CN 838 F Cl O 3-Py 839 F Cl SCH₂CO₂ H 840 F Cl SCH₂CO₂ CH₃ 841 F Cl SCH₂CO₂ C₂H₅ 842 F Cl SCH₂CO₂ Ph 843 F Cl SCH₂CO₂ CH₂Ph 844 F Cl SCH₂CO₂ Ph-4-Cl 845 F Cl SCH₂CO₂ CN 846 F Cl SCH₂CO₂ 3-Py 847 F H SCH(CH₃)CO₂ H 848 F Cl SCH(CH₃)CO₂ CH₃ 849 F Cl SCH(CH₃)CO₂ C₂H₅ 850 F Cl SCH(CH₃)CO₂ Ph 851 F Cl SCH(CH₃)CO₂ CH₂Ph 852 F Cl SCH(CH₃)CO₂ Ph-4-Cl 853 F Cl SCH(CH₃)CO₂ CN 854 F Cl SCH(CH₃)CO₂ 3-Py 855 F Cl S H 856 F Cl S CH₃ 857 F Cl S C₂H₅ 858 F Cl S Ph 859 F Cl S CH₂Ph 860 F Cl S Ph-4-Cl 861 F Cl CH═C(Cl)CO₂ H 862 F Cl CH₂CH(Cl)CO₂ H 863 Cl Cl O H 864 Cl Cl OCH₂CO₂ H 865 Cl Cl OCH(CH₃)CO₂ H 866 Cl Cl SCH₂CO₂ H 867 Cl Cl CH═C(Cl)CO₂ H 868 Cl Cl CH₂CH(Cl)CO₂ H 869 Cl Cl CO₂ H 870 H Cl O H 871 H Cl OCH₂CO₂ H 872 H Cl OCH(CH₃)CO₂ H 873 H Cl SCH₂CO₂ H 874 H Cl CH═C(Cl)CO₂ H 875 H Cl CH₂CH(Cl)CO₂ H 876 H Cl CO₂ H 877 F Cl OCH₂CO₂ Ph-4-F 878 F Cl SCH₂CO₂ Ph-4-F

TABLE 12

where A = B = N, R₄ = R₅ = H, Q = Q6 in a compound of formula I No R₁ R₂ X R₃ 879 F Cl CO₂ H 880 F Cl CO₂ CH₃ 881 F Cl CO₂ C₂H₅ 882 F Cl CO₂ Ph 883 F Cl CO₂ CH₂Ph 884 F Cl CO₂ Ph-4-Cl 885 F Cl CO₂ CN 886 F Cl CO₂ 3-Py 887 F Cl OCH₂CO₂ H 888 F Cl OCH₂CO₂ CH₃ 889 F Cl OCH₂CO₂ C₂H₅ 890 F Cl OCH₂CO₂ Ph 891 F Cl OCH₂CO₂ CH₂Ph 892 F Cl OCH₂CO₂ Ph-4-Cl 893 F Cl OCH₂CO₂ CN 894 F Cl OCH₂CO₂ 3-Py 895 F Cl OCH(CH₃)CO₂ H 896 F Cl OCH(CH₃)CO₂ CH₃ 897 F Cl OCH(CH₃)CO₂ C₂H₅ 898 F Cl OCH(CH₃)CO₂ Ph 899 F Cl OCH(CH₃)CO₂ CH₂Ph 900 F Cl OCH(CH₃)CO₂ Ph-4-Cl 901 F Cl OCH(CH₃)CO₂ CH₂Ph-4-Cl 902 F Cl OCH(CH₃)CO₂ 3-Py 903 F Cl O H 904 F Cl O CH₃ 905 F Cl O C₂H₅ 906 F Cl O Ph 907 F Cl O CH₂Ph 908 F Cl O Ph-4-Cl 909 F Cl O CN 910 F Cl O 3-Py 911 F Cl SCH₂CO₂ H 912 F Cl SCH₂CO₂ CH₃ 913 F Cl SCH₂CO₂ C₂H₅ 914 F Cl SCH₂CO₂ Ph 915 F Cl SCH₂CO₂ CH₂Ph 916 F Cl SCH₂CO₂ Ph-4-Cl 917 F Cl SCH₂CO₂ CN 918 F Cl SCH₂CO₂ 3-Py 919 F H SCH(CH₃)CO₂ H 920 F Cl SCH(CH₃)CO₂ CH₃ 921 F Cl SCH(CH₃)CO₂ C₂H₅ 922 F Cl SCH(CH₃)CO₂ Ph 923 F Cl SCH(CH₃)CO₂ CH₂Ph 924 F Cl SCH(CH₃)CO₂ Ph-4-Cl 925 F Cl SCH(CH₃)CO₂ CH₂Ph-4-Cl 926 F Cl SCH(CH₃)CO₂ 3-Py 927 F Cl S H 928 F Cl S CH₃ 929 F Cl S C₂H₅ 930 F Cl S Ph 931 F Cl S CH₂Ph 932 F Cl S Ph-4-Cl 933 F Cl CH═C(Cl)CO₂ H 934 F Cl CH₂CH(Cl)CO₂ H 935 Cl Cl O H 936 Cl Cl OCH₂CO₂ H 937 Cl Cl CH═C(Cl)CO₂ H 938 Cl Cl CH₂CH(Cl)CO₂ H 939 Cl Cl SCH₂CO₂ H 940 Cl Cl SCH(CH₃)CO₂ H 941 Cl Cl CO₂ H 942 H Cl O H 943 H Cl OCH₂CO₂ H 944 H Cl OCH(CH₃)CO₂ H 945 H Cl SCH₂CO₂ H 946 H Cl CH═C(Cl)CO₂ H 947 H Cl CH₂CH(Cl)CO₂ H 948 H Cl CO₂ H 949 F Cl OCH₂CO₂ Ph-4-F 950 F Cl SCH₂CO₂ Ph-4-F

TABLE 13

where A = B = N, R₄ = R₅ = H, Q = Q7 in a compound of formula I No R₁ R₂ X R₃  951 F Cl CO₂ H  952 F Cl CO₂ CH₃  953 F Cl CO₂ C₂H₅  954 F Cl CO₂ Ph  955 F Cl CO₂ CH₂Ph  956 F Cl CO₂ Ph-4-Cl  957 F Cl CO₂ CN  958 F Cl CO₂ 3-Py  959 F Cl OCH₂CO₂ H  960 F Cl OCH₂CO₂ CH₃  961 F Cl OCH₂CO₂ C₂H₅  962 F Cl OCH₂CO₂ Ph  963 F Cl OCH₂CO₂ CH₂Ph  964 F Cl OCH₂CO₂ Ph-4-Cl  965 F Cl OCH₂CO₂ CN  966 F Cl OCH₂CO₂ 3-Py  967 F Cl OCH(CH₃)CO₂ H  968 F Cl OCH(CH₃)CO₂ CH₃  969 F Cl OCH(CH₃)CO₂ C₂H₅  970 F Cl OCH(CH₃)CO₂ Ph  971 F Cl OCH(CH₃)CO₂ CH₂Ph  972 F Cl OCH(CH₃)CO₂ Ph-4-Cl  973 F Cl OCH(CH₃)CO₂ CH₂Ph-4-Cl  974 F Cl OCH(CH₃)CO₂ 3-Py  975 F Cl O H  976 F Cl O CH₃  977 F Cl O C₂H₅  978 F Cl O Ph  979 F Cl O CH₂Ph  980 F Cl O Ph-4-Cl  981 F Cl O CN  982 F Cl O 3-Py  983 F Cl SCH₂CO₂ H  984 F Cl SCH₂CO₂ CH₃  985 F Cl SCH₂CO₂ C₂H₅  986 F Cl SCH₂CO₂ Ph  987 F Cl SCH₂CO₂ CH₂Ph  988 F Cl SCH₂CO₂ Ph-4-Cl  989 F Cl SCH₂CO₂ CN  990 F Cl SCH₂CO₂ 3-Py  991 F H SCH(CH₃)CO₂ H  992 F Cl SCH(CH₃)CO₂ CH₃  993 F Cl SCH(CH₃)CO₂ C₂H₅  994 F Cl SCH(CH₃)CO₂ Ph  995 F Cl SCH(CH₃)CO₂ CH₂Ph  996 F Cl SCH(CH₃)CO₂ Ph-4-Cl  997 F Cl SCH(CH₃)CO₂ CH₂Ph-4-Cl  998 F Cl SCH(CH₃)CO₂ 3-Py  999 F Cl S H 1000 F Cl S CH₃ 1001 F Cl S C₂H₅ 1002 F Cl S Ph 1003 F Cl S CH₂Ph 1004 F Cl S Ph-4-Cl 1005 F Cl CH═C(Cl)CO₂ H 1006 F Cl CH₂CH(Cl)CO₂ H 1007 Cl Cl O H 1008 Cl Cl OCH₂CO₂ H 1009 Cl Cl CH═C(Cl)CO₂ H 1010 Cl Cl CH₂CH(Cl)CO₂ H 1011 Cl Cl SCH₂CO₂ H 1012 Cl Cl SCH(CH₃)CO₂ H 1013 Cl Cl CO₂ H 1014 H Cl O H 1015 H Cl OCH₂CO₂ H 1016 H Cl OCH(CH₃)CO₂ H 1017 H Cl SCH₂CO₂ H 1018 H Cl CH═C(Cl)CO₂ H 1019 H Cl CH₂CH(Cl)CO₂ H 1020 H Cl CO₂ H 1021 F Cl OCH₂CO₂ Ph-4-F 1022 F Cl SCH₂CO₂ Ph-4-F

TABLE 14

where A = B = N, R₄ = R₅ = H, Q = Q8 in a compound of formula I No R₁ R₂ X R₃ 1023 F Cl CO₂ H 1024 F Cl CO₂ CH₃ 1025 F Cl CO₂ C₂H₅ 1026 F Cl CO₂ Ph 1027 F Cl CO₂ CH₂Ph 1028 F Cl CO₂ Ph-4-Cl 1029 F Cl CO₂ CN 1030 F Cl CO₂ 3-Py 1031 F Cl OCH₂CO₂ H 1032 F Cl OCH₂CO₂ CH₃ 1033 F Cl OCH₂CO₂ C₂H₅ 1034 F Cl OCH₂CO₂ Ph 1035 F Cl OCH₂CO₂ CH₂Ph 1036 F Cl OCH₂CO₂ Ph-4-Cl 1037 F Cl OCH₂CO₂ CN 1038 F Cl OCH₂CO₂ 3-Py 1039 F Cl OCH(CH₃)CO₂ H 1040 F Cl OCH(CH₃)CO₂ CH₃ 1041 F Cl OCH(CH₃)CO₂ C₂H₅ 1042 F Cl OCH(CH₃)CO₂ Ph 1043 F Cl OCH(CH₃)CO₂ CH₂Ph 1044 F Cl OCH(CH₃)CO₂ Ph-4-Cl 1045 F Cl OCH(CH₃)CO₂ CH₂Ph-4-Cl 1046 F Cl OCH(CH₃)CO₂ 3-Py 1047 F Cl O H 1048 F Cl O CH₃ 1049 F Cl O C₂H₅ 1050 F Cl O Ph 1051 F Cl O CH₂Ph 1052 F Cl O Ph-4-Cl 1053 F Cl O CH₂Ph-4-Cl 1054 F Cl O 3-Py 1055 F Cl SCH₂CO₂ H 1056 F Cl SCH₂CO₂ CH₃ 1057 F Cl SCH₂CO₂ C₂H₅ 1058 F Cl SCH₂CO₂ Ph 1059 F Cl SCH₂CO₂ CH₂Ph 1060 F Cl SCH₂CO₂ Ph-4-Cl 1061 F Cl SCH₂CO₂ CN 1062 F Cl SCH₂CO₂ 3-Py 1063 F H SCH(CH₃)CO₂ H 1064 F Cl SCH(CH₃)CO₂ CH₃ 1065 F Cl SCH(CH₃)CO₂ C₂H₅ 1066 F Cl SCH(CH₃)CO₂ Ph 1067 F Cl SCH(CH₃)CO₂ CH₂Ph 1068 F Cl CH═C(Cl)CO₂ CN 1069 F Cl CH₂CH(Cl)CO₂ CN 1070 F Cl SCH(CH₃)CO₂ 3-Py 1071 F Cl S H 1072 F Cl S CH₃ 1073 F Cl S C₂H₅ 1074 F Cl S Ph 1075 F Cl S CH₂Ph 1076 F Cl S Ph-4-Cl 1077 F Cl CH═C(Cl)CO₂ H 1078 F Cl CH₂CH(Cl)CO₂ H 1079 Cl Cl O H 1080 Cl Cl OCH₂CO₂ H 1081 Cl Cl CH═C(Cl)CO₂ H 1082 Cl Cl CH₂CH(Cl)CO₂ H 1083 Cl Cl SCH₂CO₂ H 1084 Cl Cl SCH(CH₃)CO₂ H 1085 Cl Cl CO₂ H 1086 H Cl O H 1087 H Cl OCH₂CO₂ H 1088 H Cl OCH(CH₃)CO₂ H 1089 H Cl SCH₂CO₂ H 1090 H Cl CH═C(Cl)CO₂ H 1091 H Cl CH₂CH(Cl)CO₂ H 1092 H Cl CO₂ H 1093 F Cl OCH₂CO₂ Ph-4-F 1094 F Cl SCH₂CO₂ Ph-4-F

TABLE 15

where A = B = N, R₄ = R₅ = H, Q = Q9 in a compound of formula I No R₁ R₂ X R₃ 1095 F Cl CO₂ H 1096 F Cl CO₂ CH₃ 1097 F Cl CO₂ C₂H₅ 1098 F Cl CO₂ Ph 1099 F Cl CO₂ CH₂Ph 1100 F Cl CO₂ Ph-4-Cl 1101 F Cl CO₂ CN 1102 F Cl CO₂ 3-Py 1103 F Cl OCH₂CO₂ H 1104 F Cl OCH₂CO₂ CH₃ 1105 F Cl OCH₂CO₂ C₂H₅ 1106 F Cl OCH₂CO₂ Ph 1107 F Cl OCH₂CO₂ CH₂Ph 1108 F Cl OCH₂CO₂ Ph-4-Cl 1109 F Cl OCH₂CO₂ CN 1110 F Cl OCH₂CO₂ 3-Py 1111 F Cl OCH(CH₃)CO₂ H 1112 F Cl OCH(CH₃)CO₂ CH₃ 1113 F Cl OCH(CH₃)CO₂ C₂H₅ 1114 F Cl OCH(CH₃)CO₂ Ph 1115 F Cl OCH(CH₃)CO₂ CH₂Ph 1116 F Cl OCH(CH₃)CO₂ Ph-4-Cl 1117 F Cl OCH(CH₃)CO₂ CN 1118 F Cl OCH(CH₃)CO₂ 3-Py 1119 F Cl O H 1120 F Cl O CH₃ 1121 F Cl O C₂H₅ 1122 F Cl O Ph 1123 F Cl O CH₂Ph 1124 F Cl O Ph-4-Cl 1125 F Cl O CN 1126 F Cl O 3-Py 1127 F Cl SCH₂CO₂ H 1128 F Cl SCH₂CO₂ CH₃ 1129 F Cl SCH₂CO₂ C₂H₅ 1130 F Cl SCH₂CO₂ Ph 1131 F Cl SCH₂CO₂ CH₂Ph 1132 F Cl SCH₂CO₂ Ph-4-Cl 1133 F Cl SCH₂CO₂ CN 1134 F Cl SCH₂CO₂ 3-Py 1135 F H SCH(CH₃)CO₂ H 1136 F Cl SCH(CH₃)CO₂ CH₃ 1137 F Cl SCH(CH₃)CO₂ C₂H₅ 1138 F Cl SCH(CH₃)CO₂ Ph 1139 F Cl SCH(CH₃)CO₂ CH₂Ph 1140 F Cl SCH(CH₃)CO₂ Ph-4-Cl 1141 F Cl SCH(CH₃)CO₂ CH₂Ph-4-Cl 1142 F Cl SCH(CH₃)CO₂ 3-Py 1143 F Cl S H 1144 F Cl S CH₃ 1145 F Cl S C₂H₅ 1146 F Cl S Ph 1147 F Cl S CH₂Ph 1148 F Cl S Ph-4-Cl 1149 F Cl CH═C(Cl)CO₂ H 1150 F Cl CH₂CH(Cl)CO₂ H 1151 Cl Cl O H 1152 Cl Cl OCH₂CO₂ H 1153 Cl Cl CH═C(Cl)CO₂ H 1154 Cl Cl CH₂CH(Cl)CO₂ H 1155 Cl Cl SCH₂CO₂ H 1156 Cl Cl SCH(CH₃)CO₂ H 1157 Cl Cl CO₂ H 1158 H Cl O H 1159 H Cl OCH₂CO₂ H 1160 H Cl OCH(CH₃)CO₂ H 1161 H Cl SCH₂CO₂ H 1162 H Cl CH═C(Cl)CO₂ H 1163 H Cl CH₂CH(Cl)CO₂ H 1164 H Cl CO₂ H 1165 F Cl OCH₂CO₂ Ph-4-F 1166 F Cl SCH₂CO₂ Ph-4-F

TABLE 16

where A = B = N, R₄ = R₅ = H, Q = Q10 in a compound of formula I No R₁ R₂ X R₃ 1167 F Cl CO₂ H 1168 F Cl CO₂ CH₃ 1169 F Cl CO₂ C₂H₅ 1170 F Cl CO₂ Ph 1171 F Cl CO₂ CH₂Ph 1172 F Cl CO₂ Ph-4-Cl 1173 F Cl CO₂ CH₂Ph-4-Cl 1174 F Cl CO₂ 3-Py 1175 F Cl OCH₂CO₂ H 1176 F Cl OCH₂CO₂ CH₃ 1177 F Cl OCH₂CO₂ C₂H₅ 1178 F Cl OCH₂CO₂ Ph 1179 F Cl OCH₂CO₂ CH₂Ph 1180 F Cl OCH₂CO₂ Ph-4-Cl 1181 F Cl OCH₂CO₂ CH₂Ph-4-Cl 1182 F Cl OCH₂CO₂ 3-Py 1183 F Cl OCH(CH₃)CO₂ H 1184 F Cl OCH(CH₃)CO₂ CH₃ 1185 F Cl OCH(CH₃)CO₂ C₂H₅ 1186 F Cl OCH(CH₃)CO₂ Ph 1187 F Cl OCH(CH₃)CO₂ CH₂Ph 1188 F Cl OCH(CH₃)CO₂ Ph-4-Cl 1189 F Cl OCH(CH₃)CO₂ CH₂Ph-4-Cl 1190 F Cl OCH(CH₃)CO₂ 3-Py 1191 F Cl O H 1192 F Cl O CH₃ 1193 F Cl O C₂H₅ 1194 F Cl O Ph 1195 F Cl O CH₂Ph 1196 F Cl O Ph-4-Cl 1197 F Cl O CH₂Ph-4-Cl 1198 F Cl O 3-Py 1199 F Cl SCH₂CO₂ H 1200 F Cl SCH₂CO₂ CH₃ 1201 F Cl SCH₂CO₂ C₂H₅ 1202 F Cl SCH₂CO₂ Ph 1203 F Cl SCH₂CO₂ CH₂Ph 1204 F Cl SCH₂CO₂ Ph-4-Cl 1205 F Cl SCH₂CO₂ CH₂Ph-4-Cl 1206 F Cl SCH₂CO₂ 3-Py 1207 F H SCH(CH₃)CO₂ H 1208 F Cl SCH(CH₃)CO₂ CH₃ 1209 F Cl SCH(CH₃)CO₂ C₂H₅ 1210 F Cl SCH(CH₃)CO₂ Ph 1211 F Cl SCH(CH₃)CO₂ CH₂Ph 1212 F Cl SCH(CH₃)CO₂ Ph-4-Cl 1213 F Cl SCH(CH₃)CO₂ CH₂Ph-4-Cl 1214 F Cl SCH(CH₃)CO₂ 3-Py 1215 F Cl S H 1216 F Cl S CH₃ 1217 F Cl S C₂H₅ 1218 F Cl S Ph 1219 F Cl S CH₂Ph 1220 F Cl S Ph-4-Cl 1221 F Cl CH═C(Cl)CO₂ H 1222 F Cl CH₂CH(Cl)CO₂ H 1223 Cl Cl O H 1224 Cl Cl OCH₂CO₂ H 1225 Cl Cl CH═C(Cl)CO₂ H 1226 Cl Cl CH₂CH(Cl)CO₂ H 1227 Cl Cl SCH₂CO₂ H 1228 Cl Cl SCH(CH₃)CO₂ H 1229 Cl Cl CO₂ H 1230 H Cl O H 1231 H Cl OCH₂CO₂ H 1232 H Cl OCH(CH₃)CO₂ H 1233 H Cl SCH₂CO₂ H 1234 H Cl CH═C(Cl)CO₂ H 1235 H Cl CH₂CH(Cl)CO₂ H 1236 H Cl CO₂ H 1237 F Cl OCH₂CO₂ Ph-4-F 1238 F Cl SCH₂CO₂ Ph-4-F

TABLE 17

where A = B = N, R₄ = R₅ = H, Q = Q11 in a compound of formula I No R₁ R₂ X R₃ 1239 F Cl CO₂ H 1240 F Cl CO₂ CH₃ 1241 F Cl CO₂ C₂H₅ 1242 F Cl CO₂ Ph 1243 F Cl CO₂ CH₂Ph 1244 F Cl CO₂ Ph-4-Cl 1245 F Cl CO₂ CH₂Ph-4-Cl 1246 F Cl CO₂ 3-Py 1247 F Cl OCH₂CO₂ H 1248 F Cl OCH₂CO₂ CH₃ 1249 F Cl OCH₂CO₂ C₂H₅ 1250 F Cl OCH₂CO₂ Ph 1251 F Cl OCH₂CO₂ CH₂Ph 1252 F Cl OCH₂CO₂ Ph-4-Cl 1253 F Cl OCH₂CO₂ CH₂Ph-4-Cl 1254 F Cl OCH₂CO₂ 3-Py 1255 F Cl OCH(CH₃)CO₂ H 1256 F Cl OCH(CH₃)CO₂ CH₃ 1257 F Cl OCH(CH₃)CO₂ C₂H₅ 1258 F Cl OCH(CH₃)CO₂ Ph 1259 F Cl OCH(CH₃)CO₂ CH₂Ph 1260 F Cl OCH(CH₃)CO₂ Ph-4-Cl 1261 F Cl OCH(CH₃)CO₂ CH₂Ph-4-Cl 1262 F Cl OCH(CH₃)CO₂ 3-Py 1263 F Cl O H 1264 F Cl O CH₃ 1265 F Cl O C₂H₅ 1266 F Cl O Ph 1267 F Cl O CH₂Ph 1268 F Cl O Ph-4-Cl 1269 F Cl O CH₂Ph-4-Cl 1270 F Cl O 3-Py 1271 F Cl SCH₂CO₂ H 1272 F Cl SCH₂CO₂ CH₃ 1273 F Cl SCH₂CO₂ C₂H₅ 1274 F Cl SCH₂CO₂ Ph 1275 F Cl SCH₂CO₂ CH₂Ph 1276 F Cl SCH₂CO₂ Ph-4-Cl 1277 F Cl SCH₂CO₂ CH₂Ph-4-Cl 1278 F Cl SCH₂CO₂ 3-Py 1279 F H SCH(CH₃)CO₂ H 1280 F Cl SCH(CH₃)CO₂ CH₃ 1281 F Cl SCH(CH₃)CO₂ C₂H₅ 1282 F Cl SCH(CH₃)CO₂ Ph 1283 F Cl SCH(CH₃)CO₂ CH₂Ph 1284 F Cl SCH(CH₃)CO₂ Ph-4-Cl 1285 F Cl SCH(CH₃)CO₂ CH₂Ph-4-Cl 1286 F Cl SCH(CH₃)CO₂ 3-Py 1287 F Cl S H 1288 F Cl S CH₃ 1289 F Cl S C₂H₅ 1290 F Cl S Ph 1291 F Cl S CH₂Ph 1292 F Cl S Ph-4-Cl 1293 F Cl CH═C(Cl)CO₂ H 1294 F Cl CH₂CH(Cl)CO₂ H 1295 Cl Cl O H 1296 Cl Cl OCH₂CO₂ H 1297 Cl Cl CH═C(Cl)CO₂ H 1298 Cl Cl CH₂CH(Cl)CO₂ H 1299 Cl Cl SCH₂CO₂ H 1300 Cl Cl SCH(CH₃)CO₂ H 1301 Cl Cl CO₂ H 1302 H Cl O H 1303 H Cl OCH₂CO₂ H 1304 H Cl OCH(CH₃)CO₂ H 1305 H Cl SCH₂CO₂ H 1306 H Cl CH═C(Cl)CO₂ H 1307 H Cl CH₂CH(Cl)CO₂ H 1308 H Cl CO₂ H 1309 F Cl OCH₂CO₂ Ph-4-F 1310 F Cl SCH₂CO₂ Ph-4-F

TABLE 18

where A = B = N, R₄ = R₅ = H, Q = Q12 in a compound of formula I No R₁ R₂ X R₃ R₁₀ 1311 F Cl CO₂ H CH₃ 1312 F Cl CO₂ CH₃ CH₃ 1313 F Cl CO₂ C₂H₅ CH₃ 1314 F Cl CO₂ H NH₂ 1315 F Cl CO₂ CH₃ NH₂ 1316 F Cl CO₂ C₂H₅ NH₂ 1317 F Cl CO₂ CN NH₂ 1318 F Cl CO₂ CN CH₃ 1319 F Cl OCH₂CO₂ H CH₃ 1320 F Cl OCH₂CO₂ CH₃ CH₃ 1321 F Cl OCH₂CO₂ C₂H₅ CH₃ 1322 F Cl OCH₂CO₂ H NH₂ 1323 F Cl OCH₂CO₂ CH₃ NH₂ 1324 F Cl OCH₂CO₂ C₂H₅ NH₂ 1325 F Cl OCH₂CO₂ CN NH₂ 1326 F Cl OCH₂CO₂ CN CH₃ 1327 F Cl OCH(CH₃)CO₂ H CH₃ 1328 F Cl OCH(CH₃)CO₂ CH₃ CH₃ 1329 F Cl OCH(CH₃)CO₂ C₂H₅ CH₃ 1330 F Cl OCH(CH₃)CO₂ H NH₂ 1331 F Cl OCH(CH₃)CO₂ CH₃ NH₂ 1332 F Cl OCH(CH₃)CO₂ C₂H₅ NH₂ 1333 F Cl OCH(CH₃)CO₂ CN NH₂ 1334 F Cl O H H 1335 F Cl O H CH₃ 1336 F Cl O CH₃ CH₃ 1337 F Cl O C₂H₅ CH₃ 1338 F Cl O H NH₂ 1339 F Cl O CH₃ NH₂ 1340 F Cl O C₂H₅ NH₂ 1341 F Cl O CN NH₂ 1342 F Cl O CN CH₃ 1343 F Cl SCH₂CO₂ H CH₃ 1344 F Cl SCH₂CO₂ CH₃ CH₃ 1345 F Cl SCH₂CO₂ C₂H₅ CH₃ 1346 F Cl SCH₂CO₂ H NH₂ 1347 F Cl SCH₂CO₂ CH₃ NH₂ 1348 F Cl SCH₂CO₂ C₂H₅ NH₂ 1349 F Cl SCH₂CO₂ CN NH₂ 1350 F Cl SCH₂CO₂ CN CH₃ 1351 F H SCH(CH₃)CO₂ H CH₃ 1352 F Cl SCH(CH₃)CO₂ CH₃ CH₃ 1353 F Cl SCH(CH₃)CO₂ C₂H₅ CH₃ 1354 F Cl SCH(CH₃)CO₂ H NH₂ 1355 F Cl SCH(CH₃)CO₂ CH₃ NH₂ 1356 F Cl SCH(CH₃)CO₂ C₂H₅ NH₂ 1357 F Cl CH═C(Cl)CO₂ H NH₂ 1358 F Cl CH₂CH(Cl)CO₂ H NH₂ 1359 F Cl CH═C(Cl)CO₂ CN NH₂ 1360 F Cl CH₂CH(Cl)CO₂ CN NH₂ 1361 F Cl S H CH₃ 1362 F Cl S H NH₂ 1363 F Cl CH═C(Cl)CO₂ H CH₃ 1364 F Cl CH₂CH(Cl)CO₂ H CH₃ 1365 F Cl CH═C(Cl)CO₂ CN CH₃ 1366 F Cl CH₂CH(Cl)CO₂ CN CH₃ 1367 Cl Cl O H NH₂ 1368 Cl Cl OCH₂CO₂ H CH₃ 1369 Cl Cl OCH(CH₃)CO₂ H CH₃ 1370 Cl Cl SCH₂CO₂ H CH₃ 1371 Cl Cl CH═C(Cl)CO₂ H CH₃ 1372 Cl Cl CH₂CH(Cl)CO₂ H CH₃ 1373 Cl Cl CO₂ H CH₃ 1374 H Cl O H CH₃ 1375 H Cl OCH₂CO₂ H CH₃ 1376 H Cl OCH(CH₃)CO₂ H CH₃ 1377 H Cl SCH₂CO₂ H CH₃ 1378 H Cl CH═C(Cl)CO₂ H NH₂ 1379 H Cl CH₂CH(Cl)CO₂ H NH₂ 1380 H Cl CO₂ H NH₂ 1381 H Cl OCH₂CO₂ H NH₂ 1382 H Cl SCH₂CO₂ H NH₂

TABLE 19

where A = B = N, R₄ = R₅ = H, Q = Q13 in a compound of formula I No R₁ R₂ X R₃ R₁₀ 1383 F Cl CO₂ H CH₃ 1384 F Cl CO₂ CH₃ CH₃ 1385 F Cl CO₂ C₂H₅ CH₃ 1386 F Cl CO₂ H NH₂ 1387 F Cl CO₂ CH₃ NH₂ 1388 F Cl CO₂ C₂H₅ NH₂ 1389 F Cl CO₂ CN NH₂ 1390 F Cl CO₂ CN CH₃ 1391 F Cl OCH₂CO₂ H CH₃ 1392 F Cl OCH₂CO₂ CH₃ CH₃ 1393 F Cl OCH₂CO₂ C₂H₅ CH₃ 1394 F Cl OCH₂CO₂ H NH₂ 1395 F Cl OCH₂CO₂ CH₃ NH₂ 1396 F Cl OCH₂CO₂ C₂H₅ NH₂ 1397 F Cl OCH₂CO₂ CN NH₂ 1398 F Cl OCH₂CO₂ CN CH₃ 1399 F Cl OCH(CH₃)CO₂ H CH₃ 1400 F Cl OCH(CH₃)CO₂ CH₃ CH₃ 1401 F Cl OCH(CH₃)CO₂ C₂H₅ CH₃ 1402 F Cl OCH(CH₃)CO₂ H NH₂ 1403 F Cl OCH(CH₃)CO₂ CH₃ NH₂ 1404 F Cl OCH(CH₃)CO₂ C₂H₅ NH₂ 1405 F Cl OCH(CH₃)CO₂ CN NH₂ 1406 F Cl OCH(CH₃)CO₂ CN CH₃ 1407 F Cl O H CH₃ 1408 F Cl O CH₃ CH₃ 1409 F Cl O C₂H₅ CH₃ 1410 F Cl O H NH₂ 1411 F Cl O CH₃ NH₂ 1412 F Cl O C₂H₅ NH₂ 1413 F Cl O CN NH₂ 1414 F Cl O CN CH₃ 1415 F Cl SCH₂CO₂ H CH₃ 1416 F Cl SCH₂CO₂ CH₃ CH₃ 1417 F Cl SCH₂CO₂ C₂H₅ CH₃ 1418 F Cl SCH₂CO₂ H NH₂ 1419 F Cl SCH₂CO₂ CH₃ NH₂ 1420 F Cl SCH₂CO₂ C₂H₅ NH₂ 1421 F Cl SCH₂CO₂ CN NH₂ 1422 F Cl SCH₂CO₂ CN CH₃ 1423 F H SCH(CH₃)CO₂ H CH₃ 1424 F Cl SCH(CH₃)CO₂ CH₃ CH₃ 1425 F Cl SCH(CH₃)CO₂ C₂H₅ CH₃ 1426 F Cl SCH(CH₃)CO₂ H NH₂ 1427 F Cl SCH(CH₃)CO₂ CH₃ NH₂ 1428 F Cl SCH(CH₃)CO₂ C₂H₅ NH₂ 1429 F Cl CH═C(Cl)CO₂ H NH₂ 1430 F Cl CH₂CH(Cl)CO₂ H NH₂ 1431 F Cl CH═C(Cl)CO₂ CN NH₂ 1432 F Cl CH₂CH(Cl)CO₂ CN NH₂ 1433 F Cl S H CH₃ 1434 F Cl S H NH₂ 1435 F Cl CH═C(Cl)CO₂ H CH₃ 1436 F Cl CH₂CH(Cl)CO₂ H CH₃ 1437 F Cl CH═C(Cl)CO₂ CN CH₃ 1438 F Cl CH₂CH(Cl)CO₂ CN CH₃ 1439 Cl Cl O H NH₂ 1440 Cl Cl OCH₂CO₂ H CH₃ 1441 Cl Cl OCH(CH₃)CO₂ H CH₃ 1442 Cl Cl SCH₂CO₂ H CH₃ 1443 Cl Cl CH═C(Cl)CO₂ H CH₃ 1444 Cl Cl CH₂CH(Cl)CO₂ H CH₃ 1445 Cl Cl CO₂ H CH₃ 1446 H Cl O H CH₃ 1447 H Cl OCH₂CO₂ H CH₃ 1448 H Cl OCH(CH₃)CO₂ H CH₃ 1449 H Cl SCH₂CO₂ H CH₃ 1450 H Cl CH═C(Cl)CO₂ H NH₂ 1451 H Cl CH₂CH(Cl)CO₂ H NH₂ 1452 H Cl CO₂ H NH₂ 1453 H Cl OCH₂CO₂ H NH₂ 1454 H Cl SCH₂CO₂ H NH₂

TABLE 20

where A = B = N, R₄ = R₅ = H, R₁₁ = CH₃, Q = Q14 in a compound of formula I No R₁ R₂ X R₃ R₁₀ 1455 F Cl CO₂ H CH₃ 1456 F Cl CO₂ CH₃ CH₃ 1457 F Cl CO₂ C₂H₅ CH₃ 1458 F Cl CO₂ H NH₂ 1459 F Cl CO₂ CH₃ NH₂ 1460 F Cl CO₂ C₂H₅ NH₂ 1461 F Cl CO₂ CN NH₂ 1462 F Cl CO₂ CN CH₃ 1463 F Cl OCH₂CO₂ H CH₃ 1464 F Cl OCH₂CO₂ CH₃ CH₃ 1465 F Cl OCH₂CO₂ C₂H₅ CH₃ 1466 F Cl OCH₂CO₂ H NH₂ 1467 F Cl OCH₂CO₂ CH₃ NH₂ 1468 F Cl OCH₂CO₂ C₂H₅ NH₂ 1469 F Cl OCH₂CO₂ CN NH₂ 1470 F Cl OCH₂CO₂ CN CH₃ 1471 F Cl OCH(CH₃)CO₂ H CH₃ 1472 F Cl OCH(CH₃)CO₂ CH₃ CH₃ 1473 F Cl OCH(CH₃)CO₂ C₂H₅ CH₃ 1474 F Cl OCH(CH₃)CO₂ H NH₂ 1475 F Cl OCH(CH₃)CO₂ CH₃ NH₂ 1476 F Cl OCH(CH₃)CO₂ C₂H₅ NH₂ 1477 F Cl OCH(CH₃)CO₂ CN NH₂ 1478 F Cl OCH(CH₃)CO₂ CN CH₃ 1479 F Cl O H CH₃ 1480 F Cl O CH₃ CH₃ 1481 F Cl O C₂H₅ CH₃ 1482 F Cl O H NH₂ 1483 F Cl O CH₃ NH₂ 1484 F Cl O C₂H₅ NH₂ 1485 F Cl O CN NH₂ 1486 F Cl O CN CH₃ 1487 F Cl SCH₂CO₂ H CH₃ 1488 F Cl SCH₂CO₂ CH₃ CH₃ 1489 F Cl SCH₂CO₂ C₂H₅ CH₃ 1490 F Cl SCH₂CO₂ H NH₂ 1491 F Cl SCH₂CO₂ CH₃ NH₂ 1492 F Cl SCH₂CO₂ C₂H₅ NH₂ 1493 F Cl SCH₂CO₂ CN NH₂ 1494 F Cl SCH₂CO₂ CN CH₃ 1495 F H SCH(CH₃)CO₂ H CH₃ 1496 F Cl SCH(CH₃)CO₂ CH₃ CH₃ 1497 F Cl SCH(CH₃)CO₂ C₂H₅ CH₃ 1498 F Cl SCH(CH₃)CO₂ H NH₂ 1499 F Cl SCH(CH₃)CO₂ CH₃ NH₂ 1500 F Cl SCH(CH₃)CO₂ C₂H₅ NH₂ 1501 F Cl CH═C(Cl)CO₂ H NH₂ 1502 F Cl CH₂CH(Cl)CO₂ H NH₂ 1503 F Cl CH═C(Cl)CO₂ CN NH₂ 1504 F Cl CH₂CH(Cl)CO₂ CN NH₂ 1505 F Cl S H CH₃ 1506 F Cl S H NH₂ 1507 F Cl CH═C(Cl)CO₂ H CH₃ 1508 F Cl CH₂CH(Cl)CO₂ H CH₃ 1509 F Cl CH═C(Cl)CO₂ CN CH₃ 1510 F Cl CH₂CH(Cl)CO₂ CN CH₃ 1511 Cl Cl O H NH₂ 1512 Cl Cl OCH₂CO₂ H CH₃ 1513 Cl Cl OCH(CH₃)CO₂ H CH₃ 1514 Cl Cl SCH₂CO₂ H CH₃ 1515 Cl Cl CH═C(Cl)CO₂ H CH₃ 1516 Cl Cl CH₂CH(Cl)CO₂ H CH₃ 1517 Cl Cl CO₂ H CH₃ 1518 H Cl O H CH₃ 1519 H Cl OCH₂CO₂ H CH₃ 1520 H Cl OCH(CH₃)CO₂ H CH₃ 1521 H Cl SCH₂CO₂ H CH₃ 1522 H Cl CH═C(Cl)CO₂ H NH₂ 1523 H Cl CH₂CH(Cl)CO₂ H NH₂ 1524 H Cl CO₂ H NH₂ 1525 H Cl OCH₂CO₂ H NH₂ 1526 H Cl SCH₂CO₂ H NH₂

TABLE 21

where A = B = N, R₄ = R₅ = H, Q = Q15 in a compound of formula I No R₁ R₂ X R₃ R₁₀ 1527 F Cl CO₂ H CH₃ 1528 F Cl CO₂ CH₃ CH₃ 1529 F Cl CO₂ C₂H₅ CH₃ 1530 F Cl CO₂ H NH₂ 1531 F Cl CO₂ CH₃ NH₂ 1532 F Cl CO₂ C₂H₅ NH₂ 1533 F Cl CO₂ CN NH₂ 1534 F Cl CO₂ CN CH₃ 1535 F Cl OCH₂CO₂ H CH₃ 1536 F Cl OCH₂CO₂ CH₃ CH₃ 1537 F Cl OCH₂CO₂ C₂H₅ CH₃ 1538 F Cl OCH₂CO₂ H NH₂ 1539 F Cl OCH₂CO₂ CH₃ NH₂ 1540 F Cl OCH₂CO₂ C₂H₅ NH₂ 1541 F Cl OCH₂CO₂ CN NH₂ 1542 F Cl OCH₂CO₂ CN CH₃ 1543 F Cl OCH(CH₃)CO₂ H CH₃ 1544 F Cl OCH(CH₃)CO₂ CH₃ CH₃ 1545 F Cl OCH(CH₃)CO₂ C₂H₅ CH₃ 1546 F Cl OCH(CH₃)CO₂ H NH₂ 1547 F Cl OCH(CH₃)CO₂ CH₃ NH₂ 1548 F Cl OCH(CH₃)CO₂ C₂H₅ NH₂ 1549 F Cl OCH(CH₃)CO₂ CN NH₂ 1550 F Cl OCH(CH₃)CO₂ CN CH₃ 1551 F Cl O H CH₃ 1552 F Cl O CH₃ CH₃ 1553 F Cl O C₂H₅ CH₃ 1554 F Cl O H NH₂ 1555 F Cl O CH₃ NH₂ 1556 F Cl O C₂H₅ NH₂ 1557 F Cl O CN NH₂ 1558 F Cl O CN CH₃ 1559 F Cl SCH₂CO₂ H CH₃ 1560 F Cl SCH₂CO₂ CH₃ CH₃ 1561 F Cl SCH₂CO₂ C₂H₅ CH₃ 1562 F Cl SCH₂CO₂ H NH₂ 1563 F Cl SCH₂CO₂ CH₃ NH₂ 1564 F Cl SCH₂CO₂ C₂H₅ NH₂ 1565 F Cl SCH₂CO₂ CN NH₂ 1566 F Cl SCH₂CO₂ CN CH₃ 1567 F H SCH(CH₃)CO₂ H CH₃ 1568 F Cl SCH(CH₃)CO₂ CH₃ CH₃ 1569 F Cl SCH(CH₃)CO₂ C₂H₅ CH₃ 1570 F Cl SCH(CH₃)CO₂ H NH₂ 1571 F Cl SCH(CH₃)CO₂ CH₃ NH₂ 1572 F Cl SCH(CH₃)CO₂ C₂H₅ NH₂ 1573 F Cl CH═C(Cl)CO₂ H NH₂ 1574 F Cl CH₂CH(Cl)CO₂ H NH₂ 1575 F Cl CH═C(Cl)CO₂ CN NH₂ 1576 F Cl CH₂CH(Cl)CO₂ CN NH₂ 1577 F Cl S H CH₃ 1578 F Cl S H NH₂ 1579 F Cl CH═C(Cl)CO₂ H CH₃ 1580 F Cl CH₂CH(Cl)CO₂ H CH₃ 1581 F Cl CH═C(Cl)CO₂ CN CH₃ 1582 F Cl CH₂CH(Cl)CO₂ CN CH₃ 1583 Cl Cl O H NH₂ 1584 Cl Cl OCH₂CO₂ H CH₃ 1585 Cl Cl OCH(CH₃)CO₂ H CH₃ 1586 Cl Cl SCH₂CO₂ H CH₃ 1587 Cl Cl CH═C(Cl)CO₂ H CH₃ 1588 Cl Cl CH₂CH(Cl)CO₂ H CH₃ 1589 Cl Cl CO₂ H CH₃ 1590 H Cl O H CH₃ 1591 H Cl OCH₂CO₂ H CH₃ 1592 H Cl OCH(CH₃)CO₂ H CH₃ 1593 H Cl SCH₂CO₂ H CH₃ 1594 H Cl CH═C(Cl)CO₂ H NH₂ 1595 H Cl CH₂CH(Cl)CO₂ H NH₂ 1596 H Cl CO₂ H NH₂ 1597 H Cl OCH₂CO₂ H NH₂ 1598 H Cl SCH₂CO₂ H NH₂

TABLE 22

where A = B = N, R₄ = R₅ = H, Q = Q16 in a compound of formula I No R₁ R₂ X R₃ 1599 F Cl CO₂ H 1600 F Cl CO₂ CH₃ 1601 F Cl CO₂ C₂H₅ 1602 F Cl CO₂ Ph 1603 F Cl CO₂ CH₂Ph 1604 F Cl CO₂ Ph-4-Cl 1605 F Cl CO₂ CH₂Ph-4-Cl 1606 F Cl CO₂ 3-Py 1607 F Cl OCH₂CO₂ H 1608 F Cl OCH₂CO₂ CH₃ 1609 F Cl OCH₂CO₂ C₂H₅ 1610 F Cl OCH₂CO₂ Ph 1611 F Cl OCH₂CO₂ CH₂Ph 1612 F Cl OCH₂CO₂ Ph-4-Cl 1613 F Cl OCH₂CO₂ CH₂Ph-4-Cl 1614 F Cl OCH₂CO₂ 3-Py 1615 F Cl OCH(CH₃)CO₂ H 1616 F Cl OCH(CH₃)CO₂ CH₃ 1617 F Cl OCH(CH₃)CO₂ C₂H₅ 1618 F Cl OCH(CH₃)CO₂ Ph 1619 F Cl OCH(CH₃)CO₂ CH₂Ph 1620 F Cl OCH(CH₃)CO₂ Ph-4-Cl 1621 F Cl OCH(CH₃)CO₂ CH₂Ph-4-Cl 1622 F Cl OCH(CH₃)CO₂ 3-Py 1623 F Cl O H 1624 F Cl O CH₃ 1625 F Cl O C₂H₅ 1626 F Cl O Ph 1627 F Cl O CH₂Ph 1628 F Cl O Ph-4-Cl 1629 F Cl O CH₂Ph-4-Cl 1630 F Cl O 3-Py 1631 F Cl SCH₂CO₂ H 1632 F Cl SCH₂CO₂ CH₃ 1633 F Cl SCH₂CO₂ C₂H₅ 1634 F Cl SCH₂CO₂ Ph 1635 F Cl SCH₂CO₂ CH₂Ph 1636 F Cl SCH₂CO₂ Ph-4-Cl 1637 F Cl SCH₂CO₂ CH₂Ph-4-Cl 1638 F Cl SCH₂CO₂ 3-Py 1639 F H SCH(CH₃)CO₂ H 1640 F Cl SCH(CH₃)CO₂ CH₃ 1641 F Cl SCH(CH₃)CO₂ C₂H₅ 1642 F Cl SCH(CH₃)CO₂ Ph 1643 F Cl SCH(CH₃)CO₂ CH₂Ph 1644 F Cl SCH(CH₃)CO₂ Ph-4-Cl 1645 F Cl SCH(CH₃)CO₂ CH₂Ph-4-Cl 1646 F Cl SCH(CH₃)CO₂ 3-Py 1647 F Cl S H 1648 F Cl S CH₃ 1649 F Cl S C₂H₅ 1650 F Cl S Ph 1651 F Cl S CH₂Ph 1652 F Cl S Ph-4-Cl 1653 F Cl CH═C(Cl)CO₂ H 1654 F Cl CH₂CH(Cl)CO₂ H 1655 Cl Cl O H 1656 Cl Cl OCH₂CO₂ H 1657 Cl Cl CH═C(Cl)CO₂ H 1658 Cl Cl CH₂CH(Cl)CO₂ H 1659 Cl Cl SCH₂CO₂ H 1660 Cl Cl SCH(CH₃)CO₂ H 1661 Cl Cl CO₂ H 1662 H Cl O H 1663 H Cl OCH₂CO₂ H 1664 H Cl OCH(CH₃)CO₂ H 1665 H Cl SCH₂CO₂ H 1666 H Cl CH═C(Cl)CO₂ H 1667 H Cl CH₂CH(Cl)CO₂ H 1668 H Cl CO₂ H 1669 F Cl OCH₂CO₂ Ph-4-F 1670 F Cl SCH₂CO₂ Ph-4-F

TABLE 23

where A = R₄ = R₅ = H, A = B = N, R₁₀ = CH₃, R₁₁ = CH₃, Z = O in a compound of formula I No R₁ R₂ X Q 1671 F Cl OCH(CH₃)CO Q1 1672 F Cl OCH(CH₃)CO Q2 1673 F Cl OCH(CH₃)CO Q3 1674 F Cl OCH(CH₃)CO Q4 1675 F Cl OCH(CH₃)CO Q5 1676 F Cl OCH(CH₃)CO Q6 1677 F Cl OCH(CH₃)CO Q7 1678 F Cl OCH(CH₃)CO Q8 1679 F Cl OCH(CH₃)CO Q9 1680 F Cl OCH(CH₃)CO Q10 1681 F Cl OCH(CH₃)CO Q11 1682 F Cl OCH(CH₃)CO Q12 1683 F Cl OCH(CH₃)CO Q13 1684 F Cl OCH(CH₃)CO Q14 1685 F Cl OCH(CH₃)CO Q16 1686 F Cl OCH₂CO Q1 1687 F Cl OCH₂CO Q2 1688 F Cl OCH₂CO Q3 1689 F Cl OCH₂CO Q4 1690 F Cl OCH₂CO Q5 1691 F Cl OCH₂CO Q6 1692 F Cl OCH₂CO Q7 1693 F Cl OCH₂CO Q8 1694 F Cl OCH₂CO Q9 1695 F Cl OCH₂CO Q10 1696 F Cl OCH₂CO Q11 1697 F Cl OCH₂CO Q12 1698 F Cl OCH₂CO Q13 1699 F Cl OCH₂CO Q14 1700 F Cl OCH₂CO Q16 1701 F Cl CH₂CH(Cl)CO Q1 1702 F Cl CH₂CH(Cl)CO Q2 1703 F Cl CH₂CH(Cl)CO Q3 1704 F Cl CH₂CH(Cl)CO Q4 1705 F Cl CH₂CH(Cl)CO Q5 1706 F Cl CH₂CH(Cl)CO Q6 1707 F Cl CH₂CH(Cl)CO Q7 1708 F Cl CH₂CH(Cl)CO Q8 1709 F Cl CH₂CH(Cl)CO Q9 1710 F Cl CH₂CH(Cl)CO Q10 1711 F Cl CH₂CH(Cl)CO Q11 1712 F Cl CH₂CH(Cl)CO Q12 1713 F Cl CH₂CH(Cl)CO Q13 1714 F Cl CH₂CH(Cl)CO Q14 1715 F Cl CH₂CH(Cl)CO Q16 1716 F Cl CH═C(Cl)CO Q1 1717 F Cl CH═C(Cl)CO Q2 1718 F Cl CH═C(Cl)CO Q3 1719 F Cl CH═C(Cl)CO Q4 1720 F Cl CH═C(Cl)CO Q5 1721 F Cl CH═C(Cl)CO Q6 1722 F Cl CH═C(Cl)CO Q7 1723 F Cl CH═C(Cl)CO Q8 1724 F Cl CH═C(Cl)CO Q9 1725 F Cl CH═C(Cl)CO Q10 1726 F Cl CH═C(Cl)CO Q11 1727 F Cl CH═C(Cl)CO Q12 1728 F Cl CH═C(Cl)CO Q13 1729 F Cl CH═C(Cl)CO Q14 1730 F Cl CH═C(Cl)CO Q16 1731 F Cl CO Q1 1732 F Cl CO Q2 1733 F Cl CO Q3 1734 F Cl CO Q4 1735 F Cl CO Q5 1736 F Cl CO Q6 1737 F Cl CO Q7 1738 F Cl CO Q8 1739 F Cl CO Q9 1740 F Cl CO Q10 1741 F Cl CO Q11 1742 F Cl CO Q12 1743 F Cl CO Q13 1744 F Cl CO Q14 1745 F Cl CO Q16 1746 F Cl SCH₂CO Q1 1747 F Cl SCH₂CO Q2 1748 F Cl SCH₂CO Q3 1749 F Cl SCH₂CO Q4 1750 F Cl SCH₂CO Q5 1751 F Cl SCH₂CO Q6 1752 F Cl SCH₂CO Q7 1753 F Cl SCH₂CO Q8 1754 F Cl SCH₂CO Q9 1755 F Cl SCH₂CO Q10 1756 F Cl SCH₂CO Q11 1757 F Cl SCH₂CO Q12 1758 F Cl SCH₂CO Q13 1759 F Cl SCH₂CO Q14 1760 F Cl SCH₂CO Q16 1761 Cl Cl CH═C(Cl)CO Q1 1762 Cl Cl CH═C(Cl)CO Q3 1763 Cl Cl CH═C(Cl)CO Q6 1764 Cl Cl CH═C(Cl)CO Q7 1765 Cl Cl CH═C(Cl)CO Q8 1766 Cl Cl CH═C(Cl)CO Q10 1767 Cl Cl CH═C(Cl)CO Q11 1768 Cl Cl CH═C(Cl)CO Q12 1769 Cl Cl CH═C(Cl)CO Q16 1770 Cl Cl CH₂CH(Cl)CO Q1 1771 Cl Cl CH₂CH(Cl)CO Q3 1772 Cl Cl CH₂CH(Cl)CO Q6 1773 Cl Cl CH₂CH(Cl)CO Q7 1774 Cl Cl CH₂CH(Cl)CO Q8 1775 Cl Cl CH₂CH(Cl)CO Q10 1776 Cl Cl CH₂CH(Cl)CO Q11 1777 Cl Cl CH₂CH(Cl)CO Q12 1778 Cl Cl CH₂CH(Cl)CO Q16 1779 Cl Cl OCH₂CO Q1 1780 Cl Cl OCH₂CO Q3 1781 Cl Cl OCH₂CO Q6 1782 Cl Cl OCH₂CO Q7 1783 Cl Cl OCH₂CO Q8 1784 Cl Cl OCH₂CO Q10 1785 Cl Cl OCH₂CO Q11 1786 Cl Cl OCH₂CO Q12 1787 Cl Cl OCH₂CO Q16 1788 Cl Cl SCH₂CO Q1 1789 Cl Cl SCH₂CO Q3 1790 Cl Cl SCH₂CO Q6 1791 Cl Cl SCH₂CO Q7 1792 Cl Cl SCH₂CO Q8 1793 Cl Cl SCH₂CO Q10 1794 Cl Cl SCH₂CO Q11 1795 Cl Cl SCH₂CO Q12 1796 Cl Cl SCH₂CO Q16 1797 Cl Cl CO Q1 1798 Cl Cl CO Q3 1799 Cl Cl CO Q6 1800 Cl Cl CO Q7 1801 Cl Cl CO Q8 1802 Cl Cl CO Q10 1803 Cl Cl CO Q11 1804 Cl Cl CO Q12 1805 Cl Cl CO Q16 1806 Cl Cl OCH(CH₃)CO Q1 1807 Cl Cl OCH(CH₃)CO Q3 1808 Cl Cl OCH(CH₃)CO Q6 1809 Cl Cl OCH(CH₃)CO Q7 1810 Cl Cl OCH(CH₃)CO Q8 1811 Cl Cl OCH(CH₃)CO Q10 1812 Cl Cl OCH(CH₃)CO Q11 1813 Cl Cl OCH(CH₃)CO Q12 1814 Cl Cl OCH(CH₃)CO Q16 1815 H Cl CH═C(Cl)CO Q1 1816 H Cl CH═C(Cl)CO Q3 1818 H Cl CH═C(Cl)CO Q6 1818 H Cl CH═C(Cl)CO Q7 1819 H Cl CH═C(Cl)CO Q8 1820 H Cl CH═C(Cl)CO Q10 1821 H Cl CH═C(Cl)CO Q11 1822 H Cl CH═C(Cl)CO Q12 1823 H Cl CH═C(Cl)CO Q16 1824 H Cl CH₂CH(Cl)CO Q1 1825 H Cl CH₂CH(Cl)CO Q3 1826 H Cl CH₂CH(Cl)CO Q6 1827 H Cl CH₂CH(Cl)CO Q7 1828 H Cl CH₂CH(Cl)CO Q8 1829 H Cl CH₂CH(Cl)CO Q10 1830 H Cl CH₂CH(Cl)CO Q11 1831 H Cl CH₂CH(Cl)CO Q12 1832 H Cl CH₂CH(Cl)CO Q16 1833 H Cl OCH₂CO Q1 1834 H Cl OCH₂CO Q3 1835 H Cl OCH₂CO Q6 1836 H Cl OCH₂CO Q7 1837 H Cl OCH₂CO Q8 1838 H Cl OCH₂CO Q10 1839 H Cl OCH₂CO Q11 1840 H Cl OCH₂CO Q12 1841 H Cl OCH₂CO Q16 1842 H Cl SCH₂CO Q1 1843 H Cl SCH₂CO Q3 1844 H Cl SCH₂CO Q6 1845 H Cl SCH₂CO Q7 1846 H Cl SCH₂CO Q8 1847 H Cl SCH₂CO Q10 1848 H Cl SCH₂CO Q11 1849 H Cl SCH₂CO Q12 1850 H Cl SCH₂CO Q16 1851 H Cl CO Q1 1852 H Cl CO Q3 1853 H Cl CO Q6 1854 H Cl CO Q7 1855 H Cl CO Q8 1856 H Cl CO Q10 1857 H Cl CO Q11 1858 H Cl CO Q12 1859 H Cl CO Q16 1860 H Cl OCH(CH₃)CO Q1 1861 H Cl OCH(CH₃)CO Q3 1862 H Cl OCH(CH₃)CO Q6 1863 H Cl OCH(CH₃)CO Q7 1864 H Cl OCH(CH₃)CO Q8 1865 H Cl OCH(CH₃)CO Q10 1866 H Cl OCH(CH₃)CO Q11 1867 H Cl OCH(CH₃)CO Q12 1868 H Cl OCH(CH₃)CO Q16

TABLE 24

where R₃ = R₄ = R₅ = H, A = B = N, R₁₀ = CH₃ in a compound of formula I No R₁ R₂ X Q Salt 1869 F Cl O Q1 HCl 1870 F Cl OCH₂CO₂ Q1 HCl 1871 F Cl SCH₂CO₂ Q1 HCl 1872 F Cl CO₂ Q1 HCl 1873 F Cl CH₂CH(Cl)CO₂ Q1 HCl 1874 F Cl CH═C(Cl)CO₂ Q1 HCl 1875 F Cl OCH₂CO₂ Q1 H₃PO₄ 1876 F Cl OCH₂CO₂ Q1 CH₃CO₂H 1877 F Cl OCH₂CO₂ Q1 HCO₂CO₂H 1878 F Cl SCH₂CO₂ Q1 HCO₂CO₂H 1879 F Cl CO₂ Q1 HCO₂CO₂H 1880 F Cl CH₂CH(Cl)CO₂ Q1 HCO₂CO₂H 1881 F Cl CH═C(Cl)CO₂ Q1 HCO₂CO₂H 1882 Cl Cl O Q1 HCl 1883 Cl Cl OCH₂CO₂ Q1 HCl 1884 Cl Cl SCH₂CO₂ Q1 HCl 1885 Cl Cl CO₂ Q1 HCl 1886 Cl Cl CH₂CH(Cl)CO₂ Q1 HCl 1887 Cl Cl CH═C(Cl)CO₂ Q1 HCl 1888 Cl Cl O Q1 HCO₂CO₂H 1889 Cl Cl OCH₂CO₂ Q1 HCO₂CO₂H 1890 Cl Cl SCH₂CO₂ Q1 HCO₂CO₂H 1891 Cl Cl CO₂ Q1 HCO₂CO₂H 1892 Cl Cl CH₂CH(Cl)CO₂ Q1 HCO₂CO₂H 1893 Cl Cl CH═C(Cl)CO₂ Q1 HCO₂CO₂H 1894 H Cl O Q1 HCl 1895 H Cl OCH₂CO₂ Q1 HCl 1896 H Cl SCH₂CO₂ Q1 HCl 1897 H Cl CO₂ Q1 HCl 1898 H Cl CH₂CH(Cl)CO₂ Q1 HCl 1899 H Cl CH═C(Cl)CO₂ Q1 HCl 1900 H Cl O Q1 HCO₂CO₂H 1901 H Cl OCH₂CO₂ Q1 HCO₂CO₂H 1902 H Cl SCH₂CO₂ Q1 HCO₂CO₂H 1903 H Cl CO₂ Q1 HCO₂CO₂H 1904 H Cl CH₂CH(Cl)CO₂ Q1 HCO₂CO₂H 1905 H Cl CH═C(Cl)CO₂ Q1 HCO₂CO₂H 1906 F Cl O Q3 HCl 1907 F Cl OCH₂CO₂ Q3 HCl 1908 F Cl SCH₂CO₂ Q3 HCl 1909 F Cl CO₂ Q3 HCl 1910 F Cl CH₂CH(Cl)CO₂ Q3 HCl 1911 F Cl CH═C(Cl)CO₂ Q3 HCl 1912 F Cl O Q7 HCl 1913 F Cl OCH₂CO₂ Q7 HCl 1914 F Cl SCH₂CO₂ Q7 HCl 1915 F Cl CO₂ Q7 HCl 1916 F Cl CH₂CH(Cl)CO₂ Q7 HCl 1917 F Cl CH═C(Cl)CO₂ Q7 HCl 1918 F Cl O Q8 HCl 1919 F Cl OCH₂CO₂ Q8 HCl 1920 F Cl SCH₂CO₂ Q8 HCl 1921 F Cl CO₂ Q8 HCl 1922 F Cl CH₂CH(Cl)CO₂ Q8 HCl 1923 F Cl CH═C(Cl)CO₂ Q8 HCl 1924 F Cl O Q10 HCl 1925 F Cl OCH₂CO₂ Q10 HCl 1926 F Cl SCH₂CO₂ Q10 HCl 1927 F Cl CO₂ Q10 HCl 1928 F Cl CH₂CH(Cl)CO₂ Q10 HCl 1929 F Cl CH═C(Cl)CO₂ Q10 HCl 1930 F Cl O Q11 HCl 1931 F Cl OCH₂CO₂ Q11 HCl 1932 F Cl SCH₂CO₂ Q11 HCl 1933 F Cl CO₂ Q11 HCl 1934 F Cl CH₂CH(Cl)CO₂ Q11 HCl 1935 F Cl CH═C(Cl)CO₂ Q11 HCl 1936 Cl Cl O Q12 HCl 1937 Cl Cl OCH₂CO₂ Q12 HCl 1938 Cl Cl SCH₂CO₂ Q12 HCl 1939 Cl Cl CO₂ Q12 HCl 1940 Cl Cl CH₂CH(Cl)CO₂ Q12 HCl 1941 Cl Cl CH═C(Cl)CO₂ Q12 HCl

TABLE 25

where R₁₀ = CH₃ when Q is Q12 in a compound of formula I No R₁ R₂ X Z R₄ R₅ Q A B 1942 F Cl NH CO H H Q1 N N 1943 F Cl NH CO CH₃ CH₃ Q1 N N 1944 F Cl NH CO H SCH₃ Q1 N N 1945 F Cl NH CO H CO₂CH₃ Q1 N N 1946 F Cl NH CO Ph-4-Cl H Q1 N N 1947 F Cl NH CO CH₃ CO₂CH₃ Q1 N N 1948 F Cl NH CO H H Q1 N CH 1949 F Cl NH CO CH₃ CH₃ Q1 N CCO₂CH₃ 1950 F Cl NH CO Cl Cl Q1 N CCONMe₂ 1951 F Cl NH CO C₂H₅ CO₂CH₃ Q1 N CH 1952 F Cl NH CO CH₃ CONHPh Q1 N CH 1953 F Cl NH CO Ph-4-Cl CO₂NMe₂ Q1 N CCl 1954 F Cl NH CO H H Q1 CH N 1955 F Cl NSO₂CH₃ CO H H Q1 N N 1956 F Cl NSO₂CH₃ CO H H Q1 N CH 1957 F CN NSO₂CH₃ CO H H Q1 CH N 1958 F Cl NSO₂CF₃ CO H H Q1 N N 1959 F CN NSO₂CF₃ CO H H Q1 N CH 1960 F Cl NSO₂CF₃ CO H H Q1 CH N 1961 F Cl NSO₂CH₃ CH₂ H H Q1 N N 1962 F Cl NSO₂CH₃ CH₂ H H Q1 N CH 1963 F Cl NSO₂CH₃ CH₂ H H Q1 CH N 1964 F Cl NSO₂CF₃ CH₂ H H Q1 N N 1965 F Cl NSO₂CF₃ CH₂ H H Q1 N CH 1966 F Cl NSO₂CF₃ CH₂ H H Q1 CH N 1967 F Cl NSO₂CH₃ CO H H Q2 N N 1968 F CN NSO₂CH₃ CO H H Q2 N CH 1969 F Cl NSO₂CH₃ CO H H Q2 CH N 1970 F Cl NSO₂CF₃ CO H H Q2 N N 1971 F Cl NSO₂CF₃ CO H H Q2 N CH 1972 F CN NSO₂CF₃ CO H H Q2 CH N 1973 F Cl NSO₂CH₃ CH₂ H H Q2 N N 1974 F Cl NSO₂CH₃ CH₂ H H Q2 N CH 1975 F Cl NSO₂CH₃ CH₂ H H Q2 CH N 1976 F Cl NSO₂CF₃ CH₂ H H Q2 N N 1977 F CN NSO₂CF₃ CH₂ H H Q2 N CH 1978 F Cl NSO₂CF₃ CH₂ H H Q2 CH N 1979 F CN NSO₂CH₃ CO H H Q3 N CH 1980 F Cl NSO₂CH₃ CO H H Q3 CH N 1981 F Cl NSO₂CF₃ CO H H Q3 N N 1982 F Cl NSO₂CH₃ CH₂ H H Q3 N N 1983 F Cl NSO₂CH₃ CH₂ H H Q3 N CH 1984 F Cl NSO₂CH₃ CH₂ H H Q3 CH N 1985 F Cl NSO₂CH₃ CO H H Q7 N CH 1986 F Cl NSO₂CH₃ CO H H Q7 CH N 1987 F Cl NSO₂CH₃ CO H H Q7 N N 1988 F Cl NSO₂CH₃ CH₂ H H Q7 N N 1989 F Cl NSO₂CH₃ CH₂ H H Q7 N CH 1990 F Cl NSO₂CH₃ CH₂ H H Q7 CH N 1991 F Cl NSO₂CH₃ CO H H Q8 N N 1992 F Cl NSO₂CH₃ CO H H Q8 CH N 1993 F Cl NSO₂CH₃ CO H H Q8 N CH 1994 F Cl NSO₂CF₃ CO H H Q8 N N 1995 F Cl NSO₂CF₃ CO H H Q8 CH N 1996 F Cl NSO₂CF₃ CO H H Q8 N CH 1997 F Cl NSO₂Et CO CH₃ CH₃ Q8 N N 1998 F Cl NSO₂Et CO CH₃ CH₃ Q8 CH N 1999 F Cl NSO₂Et CO CH₃ CH₃ Q8 N CH 2000 Cl Cl NSO₂CH₃ CO H H Q8 N N 2001 Cl Cl NSO₂CH₃ CO H H Q8 CH N 2002 Cl Cl NSO₂CH₃ CO H H Q8 N CH 2003 Cl Cl NSO₂CF₃ CO H H Q8 N N 2004 Cl Cl NSO₂CF₃ CO H H Q8 CH N 2005 Cl Cl NSO₂CF₃ CO H H Q8 N CH 2006 Cl Cl NSO₂Et CO CH₃ CH₃ Q8 N N 2007 Cl Cl NSO₂Et CO CH₃ CH₃ Q8 CH N 2008 Cl Cl NSO₂Et CO CH₃ CH₃ Q8 N CH 2009 F Cl CH₂C(Cl) CO H H Q8 N N 2010 F Cl CH₂C(Cl) CO H H Q8 CH N 2011 F Cl CH₂C(Cl) CO H H Q8 N CH 2012 F Cl CH₂C(Cl) CO H H Q1 N N 2013 F Cl CH₂C(Cl) CO H H Q1 CH N 2014 F Cl CH₂C(Cl) CO H H Q1 N CH 2015 H Cl CH═C(Cl) CO H H Q1 N N 2016 F Cl OCH₂ CO H H Q1 N N 2017 F Cl SCH₂ CO H H Q3 N N 2018 F Cl CH₂C(Cl) CO H H Q10 N CH 2019 H Cl CH═C(Cl) CO H H Q10 N N 2020 F Cl OCH₂ CO H H Q10 N N 2021 F Cl SCH₂ CO H H Q10 N N 2022 F Cl CH₂C(Cl) CO H H Q11 N CH 2023 H Cl CH═C(Cl) CO H H Q11 N N 2024 F Cl OCH₂ CO H H Q11 N N 2025 F Cl SCH₂ CO H H Q11 N N 2026 F Cl CH₂C(Cl) CO H H Q12 N CH 2027 H Cl CH═C(Cl) CO H H Q12 N N 2028 F Cl OCH₂ CO H H Q12 N N 2029 F Cl SCH₂ CO H H Q12 N N 2030 F Cl CH₂C(Cl) CO H H Q16 N CH 2031 H Cl CH═C(Cl) CO H H Q16 N N 2032 F Cl OCH₂ CO H H Q16 N N 2033 F Cl SCH₂ CO H H Q16 N N 2034 F Cl NSO₂CH₃ CO H H Q7 N N 2035 F Cl NSO₂CH₃ CO H H Q10 N N 2036 F Cl NSO₂CH₃ CO H H Q11 N N 2037 F Cl NSO₂CH₃ CO H H Q12 N N 2038 F Cl NSO₂CH₃ CO H H Q16 N N 2039 F Cl NSO₂CH₃ CH₂ H H Q7 N N 2040 F Cl NSO₂CH₃ CH₂ H H Q10 N N 2041 F Cl NSO₂CH₃ CH₂ H H Q11 N N 2042 F Cl NSO₂CH₃ CH₂ H H Q12 N N 2043 F Cl NSO₂CH₃ CH₂ H H Q16 N N 2044 Cl Cl NSO₂CH₃ CO H H Q7 N N 2045 Cl Cl NSO₂CH₃ CO H H Q10 N N 2046 Cl Cl NSO₂CH₃ CO H H Q11 N N 2047 Cl Cl NSO₂CH₃ CO H H Q12 N N 2048 Cl Cl NSO₂CH₃ CO H H Q16 N N 2049 Cl Cl NSO₂CH₃ CH₂ H H Q7 N N 2050 Cl Cl NSO₂CH₃ CH₂ H H Q10 N N 2051 Cl Cl NSO₂CH₃ CH₂ H H Q11 N N 2052 Cl Cl NSO₂CH₃ CH₂ H H Q12 N N 2053 Cl Cl NSO₂CH₃ CH₂ H H Q16 N N 2054 H Cl NSO₂CH₃ CO H H Q7 N N 2055 H Cl NSO₂CH₃ CO H H Q10 N N 2056 H Cl NSO₂CH₃ CO H H Q11 N N 2057 H Cl NSO₂CH₃ CO H H Q12 N N 2058 H Cl NSO₂CH₃ CO H H Q16 N N 2059 H Cl NSO₂CH₃ CH₂ H H Q7 N N 2060 H Cl NSO₂CH₃ CH₂ H H Q10 N N 2061 H Cl NSO₂CH₃ CH₂ H H Q11 N N 2062 H Cl NSO₂CH₃ CH₂ H H Q12 N N 2063 H Cl NSO₂CH₃ CH₂ H H Q16 N N 2064 H Cl NSO₂CH₃ CO H H Q8 N N 2065 H Cl NSO₂CH₃ CO H H Q8 CH N 2066 H Cl NSO₂CH₃ CO H H Q8 N CH 2067 H Cl NSO₂CF₃ CO H H Q8 N N 2068 H Cl NSO₂CF₃ CO H H Q8 CH N 2069 H Cl NSO₂CF₃ CO H H Q8 N CH 2070 H Cl NSO₂Et CO CH₃ CH₃ Q8 N N 2071 H Cl NSO₂Et CO CH₃ CH₃ Q8 CH N 2072 H Cl NSO₂Et CO CH₃ CH₃ Q8 N CH

The compounds of formula I of the present invention can be prepared by the following processes:

Ester and Amide Linkages

For structure II and III, where X is for example CO₂, OCH(R₆)CO₂, SCH(R₆)CO₂, CH₂CH(Cl)CO₂, CH═C(Cl)CO₂ and Y is for example OH, NH₂:

Compounds II or their sodium, potassium salts are reacted with the one of the following regents: SOCl₂, (COCl)₂, COCl₂, PCl₃ or POCl₃ in a solvent such as chloroform,dichloromethane, carbon tetrachloride, hexane, benzene, toluene, tetrahydrofuran, dioxane, acetone or methyl ethyl ketone to yield an acid chloride. This acid chloride then reacted with intermediate III, (optionally in the presence of the bases such as Et₃N, pyridine, NaOH, KOH, Na₂CO₃, K₂CO₃, NaHCO₃) at a temperature from −40° C. to the boiling point of the solvent for 3 minutes to 8 hours to afford the final product I.

Intermediate II may be obtained from the ester (made by known methods such as those described in EP 0 083 055 A2) by reacting with K₂CO₃, NaOH, or KOH in ethanol, then with an inorganic acid such as hydrochloric acid.

Intermediate III (where R₃ is alkyl) may be obtained from the known reactions of an aldehyde with IV in the presence or absence of ammonium hydroxide.

Ether, Thioether, Amine Linkages

For structure II (where X is O, S, NH) and structure III (where Y═Cl, OSO₂CH₃, etc.), compounds II are reacted with the intermediates III in the presence of bases such as Et₃N, pyridine, NaOH, KOH, Na₂CO₃, K₂CO₃, NaHCO₃, NaH, NaOCH₃, NaOC₂H₅, in a solvent such as tetrahydrofuran, dioxane, acetone, methyl ethyl ketone, acetonitrile, N,N-dimethylformamide at a temperature from −40° C. to the boiling point of the solvent for 30 minutes to 18 hours to afford the final product I.

For structure II where X is for example CO₂, OCH(R₆)CO₂, SCH(R₆)CO₂, CH₂CH(Cl)CO₂ or CH═C(Cl)CO₂:

Compounds II or their sodium, potassium salts are reacted with the one of the following regents: SOCl₂, (COCl)₂, COCl₂, POCl₃ or POCl₃ in a solvent such as chloroform, dichloromethane, carbon tetrachloride, hexane, benzene, toluene, tetrahydrofuran, dioxane, acetone or methyl ethyl ketone to yield an acid chloride. This acid chloride then reacted with intermediate V, (optionally in the presence of the bases such as Et₃N, pyridine, NaOH, KOH, Na₂CO₃, K₂CO₃ or NaHCO₃) at a temperature from −40° C. to the boiling point of the solvent for 3 minutes to 8 hours to afford the final product I.

Intermediates V were prepared by known methods, for example see EP 0 567 827 A1.

The preparation of the salts of formula I, for example, is straightforward as shown:

The salts of formula I can be prepared from I in ethanol or other solvent with HCl, CH₃CO₂H, H₃PO₄, HO₂CCO₂H etc. or other acids.

The present invention now will be described in further detail with reference to Examples in order to further guide its practitioner. However, it should be understood that the present invention is by no means restricted by these specific Examples.

PREPARATION EXAMPLE A (COMPOUND NO. 15)

2-(4-Chloro-2-fluoro-5-ethoxycarbonylmethoxyphenyl)-4, 5,6,7-tetrahydro-2H-isoindole-1,3-dione (4.0 g, made substantially by the methods described in EP 0 083 055 A2) and KOH (85%, 2.1 g) in 50 ml ethanol were stirred at room temperature for 1 hour and then evaporated to dryness. To the residue was added 100 ml chloroform and 8 ml SOCl₂. The reaction mixture was then heated to reflux for 2 hours. Potassium chloride was filtered and washed with fresh chloroform. The filtrate was evaporated to dryness. To the residue was added 50 ml chloroform and 1.5 g 1-hydroxymethyl-(1H)-1,2,4-triazole. The reaction mixture was then stirred at room temperature for 5 hours. Water was added to the mixture, the organic layer was separated and washed with water and brine, dried and concentrated. The residue was purified by silica gel column chromatography to give 2.1 g of 2-(4-chloro-2-fluoro-5-[(1,2,4-triazolylmethoxy)carbonylmethoxy]phenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (Compound No. 15). M.P. 151-154° C.

PREPARATION EXAMPLE B (COMPOUND NO. 43)

2-(4-Chloro-2-fluoro-5-hydroxyphenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (4.0 g, made by substantially following the methods of EP 0 083 055 A2), K₂CO₃ in 50 ml methyl ethyl ketone and 2.0 g chloromethyl-1,2,4-triazole hydrochloride and then the mixture were heated to reflux for 5 hrs. After cooling the mixture was filtered and evaporated. Water and ethyl acetate were added to the residue. The organic layer was separated and washed with water and brine, dried and concentrated. The residue was purified by silica gel column chromatography to give 2.6 g of 2-[4-chloro-2-fluoro-5-[(1,2,4-triazol-1H-yl)methoxy]phenyl] -4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (Compound No. 43) as an oil.

¹H NMR (CDCl₃): 8.32(s,1H), 8.01(s,1H), 7.28(d,2H), 7.06(d,2H), 6.04(s,2H), 2.44(bs,4H), 1.83(bs,4H).

PREPARATION EXAMPLE C (COMPOUND NO. 1334)

To a suspension of 60% NaH(0.5 g) in 5 ml N,N-dimethylformamide was added 0.8 g of 3-[4-chloro-2-fluoro-5-hydroxyphenyl]-6-trifluoromethyl-2,4-pyrimidione (made by substantially following the methods of EP 0 255 047 A1). After 10 minutes, 0.8 g chloromethyl-1,2,4-triazole hydrochloride was added and then the mixture was heated at the bath of 80° C. for 8 hrs. After cooling, water and ethyl acetate were added to the mixture. The organic layer was separated and washed with water and brine, dried and concentrated. The residue was purified by silica gel column chromatography to give 0.75 g of 3-[4-chloro-2-fluoro-5-[(1,2,4-triazol-1H-yl)-methoxy]phenyl]-6-trifluoromethyl-2,4-pyrimidione (compound 1334), mp. 216-219° C.

¹H NMR (acetone-D₆): 8.64(s,1H), 7.96(s,1H), 7.55(d,2H), 7.52(d,2H), 6.36(s,1H), 6.27(s,2H).

PREPARATION EXAMPLE D (COMPOUND NO. 1335)

To a suspension of 60% NaH(0.08 g) in 5 ml N,N-dimethylformamide was added 0.5 g of 3-[4-chloro-2-fluoro-5-[(1,2,4-triazol-1H-yl)-methoxy]-phenyl]-6-trifluoromethyl-2,4-pyrimidione (compound 1334). After 10 minutes, 0.2 g of dimethyl sulfate was added and then the mixture was stirred at room temperature overnight. Water and ethyl acetate were added to the mixture. The organic layer was separated and washed with water and brine, dried and concentrated. The residue was purified by silica gel column chromatography to give 0.2 g of 1-methyl-3-[4-chloro-2-fluoro-5-[(1,2,4-triazol-1H-yl)methoxy]phenyl]-6-trifluoromethyl-2,4-pyrimidione (compound 1335).

¹H NMR (CDCl₃): 8.31(s,1H), 7.98(s,1H), 7.36(d,2H), 7.07(d,2H), 6.60(s,1H), 6.06(s,2H), 4.00(s,3H).

PREPARATION EXAMPLE E (COMPOUND NO. 1870)

2-[4-Chloro-2-fluoro-5-[(1,2,4-triazol-1H-yl)-methoxy]phenyl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (2.0 g) and hydrochloride acid (36%, 0.7 g) in 20 ml ethanol were stirred at room temperature for 10 minutes and then evaporated to dryness. To the residue was added 5 ml acetone and the mixture was filtered and dried to obtain 1.6 g of the hydrochloride salt of 2-[4-chloro-2-fluoro-5-[(1,2,4-triazol-1H-yl)methoxy]phenyl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (Compound No. 1870) as a solid.

¹H NMR (DMSO-D₆, 300 MHz): 8.79(s,1H), 8.12(s,1H), 7.70(d,1H), 7.28(d,1H), 6.25(s,2H), 4.96(s,2H), 2.36(bs,4H), 1.75(bs,4H).

The compounds of formula I are useful as an active ingredient for herbicides. When the compound of formula I of the present invention is used as a herbicide, the active ingredient can be used in a suitable formulation depending upon the particular purpose and by a suitable application method. Usually, the active ingredient is diluted with an inert liquid or solid carrier, and used in the form of a formulation such as a dust, a wettable powder, an emulsifiable concentrate, aqueous or oil suspension, pellets, granules, etc., If desirable one may also add a surfactant and/or other additive. Furthermore, one of ordinary skill in the art will recognize that the compound of the present invention may be used in combination with an insecticide, a nematocide, a fungicide, other herbicides, a plant growth controlling agent, a fertilizer, etc.

The compounds of the present invention can be used in the form of compositions or formulations. Examples of the preparation of compositions and formulations can be found in the American Chemical Society publication “Pesticidal Formulation Research,” (1969), Advances in Chemistry Series No. 86, written by Wade Van Valkenburg; and the Marcel Dekker, Inc. publication “Pesticide Formulations”, (1973) edited by Wade Van Valkenburg. In these compositions and formulations, the active substance is mixed with conventional inert agronomically acceptable (i.e., plant compatible and/or pesticidally inert) pesticide diluents or extenders such as solid carrier material or liquid carrier material, of the type usable in conventional pesticide compositions or formulations. By “agronomically acceptable carrier” is meant any substance which can be used to dissolve, disperse of diffuse the active ingredient in the composition without impairing the active ingredient's effectiveness and which by itself has no significant detrimental effect on the soil, equipment, desirable plants, or agronomic environment. If desired, adjuvants such as surfactants, stabilizers, antifoam agents and anti-drift agents may also be combined. Compositions and formulations according to the present invention may also include known pesticidal compounds. This expands the spectrum of activity of the preparation and may give rise to synergism.

The formulations, contain from about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s).

If the compound of formula(I) is formulated with an additional herbicide, the concentration of active ingredient(s) in the compositions can vary within a wide range, depending on the active compound, the applications for which they are destined, the environmental conditions and the kind of formulation. The concentration of active ingredient(s) in the compositions is generally between 1% to 95%, preferably between 5% to 60%.

The formulations now will be described in detail with reference to typical Formulation Examples and do not limit the scope of this invention. In the following Formulation Examples, “parts” means “parts by weight”. The compound number of the active ingredient corresponds to the one in Tables 1-24.

FORMULATION EXAMPLES 1a-c

Compound No. 1, 15 or 43 (all 50 parts), 5 parts of polyoxyethylene alkylaryl ether, 5 parts of sodium dodecylbenzenesulfate and 40 parts of synthetic hydrated silicon dioxide are well mixed while being powdered in order to obtain a 50% wettable powder.

FORMULATION EXAMPLE 2

Compound No. 35 (10 parts), 6 parts of polyoxyethylene alkylaryl ether, 4 parts of sodium dodecylbenzenesulfate, 30 parts of xylene and 50 parts of cyclohexanone are well mixed while being powdered in order to obtain a 10% by weight emulsifiable concentrate.

FORMULATION EXAMPLE 3

Compound No. 15 (20 parts), 2 parts of synthetic hydrated silicon dioxide, 3 parts of polyoxyethylene sorbitan monooleate, 5 parts of carboxymethyl cellulose and 70 parts of water are well mixed and pulverized until the particle size of the active ingredient becomes less than 5 microns in order to obtain a 20% by weight granule.

FORMULATION EXAMPLE 4

Compound No. 15 (5 parts), 1 part of isopropyl acid phosphate, 64 parts of kaolin clay and 30 parts of talc are well mixed and pulverized until the particle size of the active ingredient becomes less than 5 microns in order to obtain a 5% by weight dust.

FORMULATION EXAMPLE 5

Compound No. 15 (25 parts), 3 parts of polyoxyethylene sorbitan monooleate, 2 parts of polyvinyl alcohol and 70 parts of water are well mixed and pulverized until the particle size of the active ingredient becomes less than 5 microns in order to obtain a 25% an aqueous suspension.

The effective dose of the compounds of the present invention is usually within a range of from 1 g/ha to 3 kg/ha, preferably from 5 g/ha to 500 g/ha.

Biological Testing

The herbicidal activity of compounds of formula (I) with respect to weeds such as Bidens pilosa (beggartick, BID), Solanum nigrum (nightshade, NS), Polygonum lapathifolium (smartweed, SMT), Abutilon theophrasti (velvetleaf, VEL) was evaluated.

For each compounds, the evaluation tests were carried out according to the following operating procedures.

For preemergence tests, immediately after planting, the test compound was sprayed directly onto the soil surface. The flats or pots were placed in the greenhouse and then watered. For postemergence tests, the seeds were allowed to germinate and grow for 10 to 21 days. Before application, each series of development. The test plants were selected for uniformity, size and stage of development. The test plants were then treated with the test compound, returned to the greenhouse and watered. The plants not treated with the compound under evaluation were used as a comparison.

The compound to be evaluated was dissolved in an appropriate solvent, usually acetone, or the formulation of the evaluated compounds was added to the water, and sprayed over the flats or pots using a carrier volume equivalent to 187 or 468 liters per hectare at the rate of application in grams per hectare (g/ha). About two or four week s after application of the test compounds, the state of the plant was observed. Each species was evaluated on a scale of 0-100 in which 0 equals no activity and 100 equals total control. Some of the test results are shown in Table 26.

TABLE 26 Compound Type g/ha BID NS SMT VEL 15 POST 150 60 100 40 100 43 POST 1200 100 100 100 100 

We claim:
 1. A compound represented by formula I

wherein R₁ is selected from H, F, Br, Cl, NO₂ and CN; R₂ is selected from F, Cl, Br, H and CN; R₃ is selected from H and CN; and alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, cycloalkanyl, haloalkenyl, haloalkynyl, alkoxy, alkylthio, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl, aryl, arylalkyl, heteroaryl and heteroarylalkyl, all of which may be further substituted; R₄ and R₅ are each independently selected from H, halo and CN; and alkyl, cycloalkyl, haloalkyl, alkoxy, alkylthio, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl, CO₂R₆, CONR₆R₁₃, OR₆, SR_(6, SO) ₂R₆, NR₆R₁₃, SO₂NR₆R₁₃, aryl, arylalkyl, heteroaryl and heteroarylalkyl, all of which may be further substituted; R₆ is selected from H, alkyl, cycloalkyl, alkoxy, alkylthio, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfinylcycloalkyl, alkylsulfinylcycloalkyl, aryl and arylalkyl, all of which may be further substituted; R₇ is selected from H, alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl and COR₉, all of which may be further substituted; R₈ is selected from alkyl, haloalkyl, cycloalkyl, cycloalkenyl, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl, aryl and arylalkyl; R₉ is selected from H, alkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl, alkenyl, alkynyl, haloalkyl and cycloalkyl, all of which may be further substituted; R₁₀ is selected from H, halo, NH₂, alkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl, haloalkyl, CN, CO₂(alkyl), CONH(alkyl), CON(alkyl)₂ wherein each alkyl may be the same or different, CH₃CN, CH₂CH═CH₂, CH₂C≡CH, CH₂CO₂(alkyl), CH₂OCH₃ and CH₂-1,2,4triazole, all of which may be further substituted; R₁₁ is selected from H, CN, alkyl, haloalkyl and CO₂(alkyl); R₁₂ is selected from H, alkyl, CO₂R₆, CONR₆R₁₃, OR₆, SR₆, SO₂R₆, SO₃NR₆R₁₃ and NR₆R₁₃; R₁₃ is H, alkyl, aryl or arylalkyl; A is N; B is N; Z is O, CH(R₃), CO, CS, CONR₁₂ or CSNR₁₂; X is selected from O, S, NR₁₂, CO₂, OCH(R₆)CO₂, SCH(R₆)CO₂, CH═C(halo)CO₂, CH₂CH(halo)CO₂, CONH, OCH(R₆)CONH, SCH(R₆)CONH, CH═C(halo)CONH and CH₂CH(halo)CONH when Z is CH(R₃); X is selected from CO, OCH(R₆)CO, SCH(R₆)CO, CH═C(halo)CO and CH₂CH(halo)CO when Z is O; X is selected from O, S, CO, OCH(R₆), CH═C(halo), CH₂CH(halo), CONH, OCH(R₆)CONH, SCH(R₆)CONH, CH═C(halo)CONH, CH₂CH(halo)CONH and NR₁₂ when Z is CO, CS, CONR₁₂ or CSNR₁₂; and Q is selected from NR₇COR₈, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q14, Q15 and Q16 wherein Q2 is 5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one-1-yl, Q3 is 5,6,7,8-tetrahydro-1H,3H-[1, 3,4]thiadiazolo[3,5-a]pyridazineimin-1-yl, Q4 is 4,3,5,6,7-tetrahydroimidazo[1,5-a]pyridine-1,3(2H,5H)-dione-2yl, Q5 is 1,6,8-triazabicyclo[4,3,0]-nonane-7,9-dion-8-yl, Q6 is 5-(1-methyethylidene)-2,4oxazolidinedione-3-yl, Q7 is 5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2(3H)-one-3-yl, Q8 is 4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one-1-yl, Q9 is 2-methyl-1,2,4-oxadiazolidine-3,5-dione-4-yl, Q10 is 4-chloro-1-methyl-5-difluoromethoxy-1H-pyrazol-3-yl, Q11 is 4-bromo-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl, Q12 is 1-substituted-6-trifluoromethyl-2,4-pyrimidione-3-yl, Q13 is 1-substituted-6-trifluoromethyl-1,3,5-triazine-2,4-dione-1-yl, Q14 is 4,5-disubstituted-4,5-dihydro-1,2,4-triazine-3(2H)-one-2-yl, Q15 is 4-substituted-1,2,4-triazine-3,5(2H,4H)-dione-2-yl and Q16 is 5-methyl-6-oxo-4-(trifluoromethyl)-6H-pyridazin-1-yl; or the agronomically acceptable salts thereof.
 2. The compound of claim 1 wherein R₁ is selected from H, F, Br, Cl, NO₂ and CN; R₂ is selected from F, Cl, Br, H and CN; R₃ is selected from H, CN and halo; and (C₁-C₁₂)alkyl, cyclo(C₃-C₈)alkyl, (C₂-C₁₂)alkenyl, cyclo(C₃-C₈)alkenyl, (C₂-C₁₂)alkynyl, halo(C₁-C₁₂)alkyl, halo(C₂-C₁₂)alkenyl, halo(C₂-C₁₂)alkynyl, (C₁-C₁₂)alkoxy, (C₁-C₁₂)alkylthio, (C₁-C₁₂)alkylsulfonyl(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfinyl(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfonylcyclo(C₃-C₈)alkyl, (C₁-C₁₂)alkylsulfinylcyclo(C₃-C₈)alkyl, cyano(C₁-C₁₂)alkoxy, cyano(C₁-C₁₂)alkyl, cyanocyclo(C₃-C₈)alkyl, halo(C₁-C₁₂)alkoxy, halo(C₁-C₁₂)alkylthio, halocyclo(C₃-C₈)alkyl, aryl, heteroaryl, aryl(C₁-C₁₂)alkyl and heteroaryl(C₂-C₁₂)alkyl, all of which may be further substituted with from one to three substituents independently selected from bromo, chloro, fluoro, (C₁-C₁₂)alkyl, cyclo(C₃-C₈)alkyl, (C₂-C₁₂)alkenyl, cyclo(C₃-C₈)alkenyl, (C₂-C₁₂)alkynyl, halo(C₁-C₁₂)alkyl, halo(C₂-C₁₂)alkenyl, halo(C₂-C₁₂)alkynyl, (C₁-C₁₂)alkoxy, (C₁-C₁₂)alkylthio, (C₁-C₁₂)alkylsulfonyl, (C₁-C₁₂)alkylsulfinyl, phenyl, phen(C₁-C₁₂)alkyl, phen(C₂-C₁₂)alkenyl, phen(C₂-C₁₂)alkynyl, cyano, halo(C₁-C₁₂)alkoxy, 1,3-dioxalan-2-yl and nitro; R₄ and R₅ are each independently selected from H, halo and CN; and (C₁-C₁₂)alkyl, cyclo(C₃-C₈)alkyl, halo(C₁-C₁₂)alkyl, (C₁-C₁₂)alkoxy, (C₁-C₁₂)alkylthio, (C₁-C₁₂)alkylsulfonyl (C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfinyl(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfonylcyclo(C₃-C₈)alkyl, (C₁-C₁₂)alkylsulfinylcyclo(C₃-C₈)alkyl, cyano(C₁-C₁₂)alkoxy, cyano(C₁-C₁₂)alkyl, cyanocyclo(C₃-C₈)alkyl, halo(C₁-C₁₂)alkoxy, halo(C₁-C₁₂)alkylthio, halocyclo(C₃-C₈)alkyl, CO₂R₆, CONHR₆, CON((C₁-C₁₂)alkyl)R₆, OR₆, SR₆, SO₂R₆, NHR₆, N((C₁-C₁₂)alkyl)R₆, SO₂N((C₁-C₁₂)alkyl)R₆, aryl, heteroaryl, aryl(C₁-C₁₂)alkyl and heteroaryl(C₂-C₁₂)alkyl, all of which may be further substituted with from one to three substituents independently selected from bromo, chloro, fluoro, (C₁-C₁₂)alkyl, cyclo(C₃-C₈)alkyl, (C₂-C₁₂)alkenyl, cyclo(C₃-C₈)alkenyl, (C₂-C₁₂)alkynyl, halo(C₁-C₁₂)alkyl, halo(C₂-C₁₂)alkenyl, halo(C₂-C₁₂)alkynyl, (C₁-C₁₂)alkoxy, (C₁-C₁₂)alkylthio, (C₁-C₁₂)alkylsulfonyl, (C₁-C₁₂)alkylsulfinyl, phenyl, phen(C₁-C₁₂)alkyl phen(C₂-C₁₂)alkenyl, phen(C₂-C₁₂)alkynyl, cyano, halo(C₁-C₁₂)alkoxy, 1,3-dioxalan-2-yl and nitro; R₆, is selected from H, (C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfonyl(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfinyl(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfonylcyclo(C₃-C₈)alkyl, (C₁-C₁₂)alkylsulfinylcyclo(C₃-C₈)alkyl, cyano(C₁-C₁₂)alkoxy, cyano(C₁-C₁₂)alkyl, cyanocyclo(C₃-C₈)alkyl, halo(C₁-C₁₂)alkoxy, halo(C₁-C₁₂)alkylthio, halocyclo(C₃-C₈)alkyl, aryl and aryl(C₁-C₁₂)alkyl; R₇ is selected from H, (C₁-C₁₂)alkyl, cyclo(C₃-C₈)alkyl, halo(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfonyl(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfinyl(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfonylcyclo(C₃-C₈)alkyl, (C₁-C₁₂)alkylsulfinylcyclo(C₃-C₈)alkyl, cyano(C₁-C₁₂)alkoxy, cyano(C₁-C₁₂)alkyl, cyanocyclo(C₃-C₈)alkyl, halo(C₁-C₁₂)alkoxy, halo(C₁-C₁₂)alkylthio, halocyclo(C₃-C₈)alkyl and COR₉; R₈ is selected from (C₁-C₁₂)alkyl, cyclo(C₃-C₈)alkyl, cyclo(C₃-C₈)alkenyl, halo(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfonyl (C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfinyl(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfonylcyclo(C₃-C₈)alkyl, (C₁-C₁₂)alkylsulfinylcyclo(C₃-C₈)alkyl, cyano (C₁-C₁₂)alkoxy, cyano(C₁-C₁₂)alkyl, cyanocyclo(C₃-C₈)alkyl, halo(C₁-C₁₂)alkoxy, halo(C₁-C₁₂)alkylthio, halocyclo(C₃-C₈)alkyl, aryl and aryl(C₁-C₁₂)alkyl; R₉ is selected from H, (C₁-C₁₂)alkyl, (C₂-C₁₂)alkenyl, cyclo(C₃-C₈)alkyl, halo(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfonyl(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfinyl(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfonylcyclo(C₃-C₈)alkyl, (C₁-C₁₂)alkylsulfinylcyclo(C₃-C₈)alkyl, cyano(C₁-C₁₂)alkoxy, cyano(C₁-C₁₂)alkyl, cyanocyclo(C₃-C₈)alkyl, halo(C₁-C₁₂)alkoxy, halo(C₁-C₁₂)alkylthio and halocyclo(C₃-C₈)alkyl; R₁₀ is selected from H, chloro, NH₂, (C₁-C₁₂)alkyl, halo(C₁-C₁₂)alkyl, CN, (C₁-C₁₂)alkylsulfonyl(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfinyl(C₁-C₁₂)alkyl, (C₁-C₁₂)alkylsulfonylcyclo(C₃-C₈)alkyl, (C₁-C₁₂)alkylsulfinylcyclo(C₃-C₈)alkyl, cyano(C₁-C₁₂)alkoxy, cyano(C₁-C₁₂)alkyl, cyanocyclo(C₃-C₈)alkyl, halo(C₁-C₁₂)alkoxy, halo(C₁-C₁₂)alkylthio, halocyclo(C₃-C₈)alkyl, CO₂(C₁-C₁₂)alkyl, CONH(C₁-C₁₂)alkyl, CON((C₁-C₁₂)alkyl)₂, CH₂CN, CH₂CH═CH₂, CH₂C≡CH, CH₂CO₂(C₁-C₁₂)alkyl, CH₂OCH₃, CH₂-1,2,4-triazole; R₁₁ is selected from H, CN, (C₁-C₁₂)alkyl, halo(C₁-C₁₂)alkyl and CO₂(C₁-C₁₂)alkyl; R₁₂ is selected from H, (C₁-C₁₂)alkyl, CO₂R₆, CON(((C₁-C₁₂)alkyl)R₆, OR₆, SR₆, SO₂R₆, SO₂N((C₁-C₁₂)alkyl)R₁₃, and N((C₁-C₁₂)alkyl)R₁₃; R₁₃ is H, (C₁-C₁₂)alkyl, aryl or aryl(C₁-C₁₂)alkyl; A is N; B is N; Z is O, CH(R₃), CO, CS, CONR₁₂ or CSNR₁₂; X is selected from O, S, NR₁₂, CO₂, OCH(R₆)CO₂, SCH(R₆)CO₂, CH═C(Cl)CO₂, CH₂CH(Cl)CO₂, CONH, OCH(R₆)CONH, SCH(R₆)CONH, CH═C(Cl)CONH and CH₂CH(Cl)CONH when Z is CH(R₉); X is selected from CO, OCH(R₆)CO, SCH(R₆)CO, CH═C(Cl)CO, CH₂CH(Cl)CO when Z is O; X is selected from O, S, CO, OCH(R₆), CH═C(Cl), CH₂CH(Cl), CONH, OCH(R₆)CONH, SCH(R₆)CONH, CH═C(Cl)CONH, CH₂CH(Cl)CONH and NR₁₂ when Z is CO, CS, CONR₁₂ or CSNR₁₂; Q is selected from NR₇COR₈, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q14, Q15 and Q16; or the agronomically acceptable salts thereof.
 3. The compound of claim 2 wherein R₁ is H, F or Cl; R₂ is Cl; R₃ is selected from H, bromo, chloro, fluoro, (C₁-C₆)alkyl, cyclo(C₅-C₆)alkyl, (C₂-C₆)alkenyl, cyclo(C₃-C₈)alkenyl, (C₂-C≢)alkynyl, halo(C₁-C₆)alkyl, halo(C₂-C₆)alkenyl, halo(C₂-C₆)alkynyl, (C₁-C₆)alkoxy, (C₁-C₆)alkylthio, aryl, heteroaryl, aryl(C₁-C₁₂)alkyl and heteroaryl(C₂ C₁₂)alkyl wherein the aryl or heteroaryl group is selected from furan, naphthalene, phenyl, pyrazole, pyridine, pyrimidine, thiophene and triazole, said aryl and heteroaryl group may be further substituted with from one to three substituents independently selected from bromo, chloro, fluoro, (C₁-C₁₂)alkyl, cyclo(C₃-C₈)alkyl, (C₂-C₁₂)alkenyl, cyclo(C₃-C₈)alkenyl, (C₂-C₁₂)alkynyl, halo(C₁-C₁₂)alkyl, halo(C₂-C₁₂)alkenyl, halo(C₂-C₁₂)alkynyl, (C₁-C₁₂)alkoxy, (C₁-C₁₂)alkylthio, (C₁-C₁₂)alkylsulfonyl, (C₁-C₁₂)alkylsulfinyl, phenyl, phen(C₁-C₁₂)alkyl, phen(C₂-C₁₂)alkenyl, phen(C₂-C₁₂)alkynyl, cyano, halo(C₁-C₁₂)alkoxy, 1,3-dioxalan-2-yl and nitro; R₄ and R₅ are each independently selected from H, bromo, chloro, fluoro, CN, (C₁-C₆)alkyl, cyclo(C₅-C₆)alkyl, halo(C₁-C₆)alkyl, (C₁-C₆)alkoxy, (C₁-C₆)alkylthio, CO₂R₆CONHR₆, CON((C₁-C₁₂)alkyl)R₆, OR₆, SR₆, SO₂R₆, NHR₆, N((C₁-C₁₂)alkyl)R₆, SO₂N((C₁-C₁₂)alkyl)R₆, aryl, heteroaryl, aryl(C₁-C₁₂)alkyl and heteroaryl(C₂-C₁₂)alkyl, wherein the aryl or heteroaryl group is selected from furan, naphthalene, phenyl, pyrazole, pyridine, pyrimidine, thiophene and triazole, said aryl and heteroaryl group may be further substituted with from one to three substituents independently selected from bromo, chloro, fluoro, (C₁-C₁₂)alkyl, cyclo(C₃-C₈)alkyl, (C₂-C₁₂)alkenyl, cyclo(C₃-C₈)alkenyl, (C₂-C₁₂)alkynyl, halo(C₁-C₁₂)alkyl, halo(C₂-C₁₂)alkenyl, halo(C₂-C₁₂)alkynyl, (C₁-C₁₂)alkoxy, (C₁-C₁₂)alkylthio, (C₁-C₁₂)alkylsulfonyl, (C₁-C₁₂)alkylsulfinyl, phenyl, phen(C₁-C₁₂)alkyl, phen(C₂-C₁₂)alkenyl, phen(C₂-C₁₂)alkynyl, cyano, halo(C₁-C₁₂)alkoxy, 1,3-dioxalan-2-yl and nitro; R₆ is selected from H, (C₁-C₁₂)alkyl, aryl and aryl(C₁-C₆)alkyl, where the aryl group is naphthyl or phenyl; R₇ is selected from H, (C₁-C₁₂)alkyl, cyclo(C₃-C₈)alkyl, halo(C₁-C₁₂)alkyl and COR₉; R₈ is selected from (C₁-C₁₂)alkyl, cyclo(C₃-C₈)alkyl, cyclo(C₃-C₈)alkenyl, halo(C₁-C₁₂)alkyl, aryl and aryl(C₁-C₆)alkyl; R₉ is selected from H, (C₁-C₆)alkyl, (C₂-C₁₂)alkenyl, (C₂-C₆)alkenyl, cyclo(C₃-C₈)alkyl, cyclo(C₅-C₆)alkyl, halo(C₁-C₁₂)alkyl, halo(C₁-C₆)alkyl; R₁₀ is selected from H, chloro, NH₂, (C₁-C₆)alkyl, halo(C₁-C₁₂)alkyl, halo(C₁-C₆)alkyl, CN, CO₂(C₁-C₁₂)alkyl, CONH(C₁-C₁₂)alkyl, CON((C₁-C₁₂)alkyl)₂, CH₂CN, CH₂CH═CH₂, CH₂C≡CH, CH₂CO₂(C₁-C₁₂)alkyl, CH₂OCH₃, CH₂-1,2,4-triazole; R₁₁ is selected from H, CN, (C₁-C₆)alkyl, halo(C₁-C₁₂)alkyl, halo(C₁-C₆)alkyl and CO₂(C₁-C₁₂)alkyl; R₁₂ is selected from H, (C₁-C₈)alkyl, CO₂R₆, CON((C₁-C₈)alkyl)R₆, OR₆, SR₆, SO₂R₆, SO₂N((C₁-C₈)alkyl)R₁₃; and N((C₁-C₈)alkyl)R₁₃; R₁₃ is H, (C₁-C₈)alkyl, aryl or aryl(C₁-C₆)alkyl where the aryl group is naphthyl or phenyl; A is N; B is N; Z is O, CH(R₃), CO, CS, CONR₁₂ or CSNR₁₂; X is selected from O, S, NH, CO₂, OCH(R₆)CO₂, SCH(R₆)CO₂, CH═C(Cl)CO₂, CH₂CH(Cl)CO₂, CONH, OCH(R₆)CONH, SCH(R₆)CONH, CH═C(Cl)CONH and CH₂CH(Cl)CONH when Z is CH(R₃); X is selected from CO, OCH(R₆)CO, SCH(R₆)CO, CH═C(Cl)CO and CH₂CH(Cl)CO when Z is O; X is selected from O, S, CO, OCH(R₆), CH═C(Cl), CH₂CH(Cl), CONH, OCH(R₆)CONH, SCH(R₆)CONH, CH═C(Cl)CONH, CH₂CH(Cl)CONH and NR₁₂ when Z is CO, CS, CONR₁₂ or CSNR₁₂; Q is NR₇COR₈, or selected from Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q14, Q15 and Q16; or the agronomically acceptable salts thereof selected from those formed from hydrochloric acid, sulfuric acid, acetic acid, propionic acid, phosphoric acid and oxalic acid.
 4. The compound of claim 3 wherein R₁ is H, F or Cl; R₂ is Cl; R₃ is selected from H, bromo, chloro, fluoro, (C₁-C₆)alkyl, cyclo(C₅-C₆)alkyl, (C₂-C₆)alkenyl, cyclo(C₃-C₈)alkenyl, (C₂-C₆)alkynyl halo(C₁-C₆)alkyl, halo(C₂-C₆)alkenyl, halo(C₂-C₆)alkynyl, (C₁-C₆)alkoxy, (C₁-C₆)alkylthio, 3-furyl, 4-chloro-2-furyl, 5-chloro-2-furyl, 5-chloro3-furyl, 2,5-dichloro-3-furyl, 1-naphthyl, 2-naphthyl, phenyl, 4-methylphenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-fluorophenyl, 4-chlorophenyl, 4-trifluoromethylphenyl, 4bromophenyl, 4-chlorophenyl, 3-fluorophenyl, 4-trifluoromethoxyphenyl, 4-cyanophenyl, 3-(1,3-dioxolan-2-yl)phenyl, 2-fluorophenyl, 2-chlorophenyl, 2-trifluoromethoxyphenyl, 3,5-difluorophenyl, 3,6-dichlorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 3-chloro-4-fluorophenyl, 3,4-difluorophenyl, 3-fluoro-5-trifluoromethylphenyl, 3,4,5-trifluorophenyl, 2-pyridyl, 4-chloro-2-pyridyl, 6-chloro-2-pyridyl, 4,6-dichloro-2-pyridyl, 3-pyridyl, 5-bromo-3-pyridyl, 5,6-dichloro-3-pyridyl, 5-chloro.3-pyridyl, 5-fluoro-3-pyridyl, 4-pyridyl, 2-fluoro-4-pyridyl, 2-chloro-4-pyridyl, 2-chloro-6-methyl-4-pyridyl, 2-methyl-4-pyridyl, 2-methoxy-4-pyridyl, 2-cyano-4-pyridyl, 2,6-difluoro-4-pyridyl, 2, 6-dichloro-4-pyridyl, 2-thienyl, 3-thienyl, 4-chloro-2-thienyl, 5-chloro-2-thienyl, 5-chloro-3-thienyl and 2,5-dichloro-3-thienyl; R₄ and R₅ are each independently selected from H, bromo, chloro, fluoro, CN, (C₁-C₆)alkyl, cyclo(C₅-C₆)alkyl, halo(C₁-C₆)alkyl, (C₁-C₆)alkoxy, (C₁-C₆)alkylthio, CO₂R₆, CONHR₆, CON((C₁-C₆)alkyl)R₆, OR₆, SR₆, SO₂R₆, NHR₆, 3-furyl, 4-chloro-2-furyl, 5-chloro-2-furyl, 5-chloro-3-furyl, 2,5-dichloro-3-furyl, 1-naphthyl, 2-naphthyl, phenyl, 4-methylphenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-fluorophenyl, 4-chlorophenyl, 4-trifluoromethylphenyl, 4-bromophenyl, 4-chlorophenyl, 3-fluorophenyl, 4-trifluoromethoxyphenyl, 4-cyanophenyl, 3-(1,3-dioxolan-2-yl)phenyl, 2-fluorophenyl, 2-chlorophenyl, 2-trifluoromethoxyphenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 3-chloro-4-fluorophenyl, 3,4-difluorophenyl, 3-fluoro-5-trifluoromethylphenyl, 3,4,5-trifluorophenyl, 2-pyridyl, 4-chloro-2-pyridyl, 6-chloro-2-pyridyl, 4,6-dichloro-2-pyridyl, 3-pyridyl, 5-bromo-3-pyridyl, 5,6-dichloro-3-pyridyl, 5-chloro-3-pyridyl, 5-fluoro-3-pyridyl, 4-pyridyl, 2-fluoro-4-pyridyl, 2-chloro-4-pyridyl, 2-chloro-6-methyl-4-pyridyl, 2-methyl-4-pyridyl, 2-methoxy-4-pyridyl, 2-cyano-4-pyridyl, 2,6-difluoro-4pyridyl 2,6-dichloro-4-pyridyl, 2-thienyl, 3-thienyl, 4-chloro-2-thienyl, 5-chloro-2-thienyl, 5-chloro-3-thienyl and 2,5-dichloro-3thienyl; R₆ is selected from H, (C₁-C₆)alkyl, 1-naphthyl, 2-naphthyl, phenyl, 4-methylphenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-fluorophenyl, 4-chlorophenyl, 4trifluoromethylphenyl, 4-bromophenyl, 4-chlorophenyl, 3-fluorophenyl, 4-trifluoromethoxyphenyl, 4-cyanophenyl, 3-(1,3-dioxolan-2-yl)phenyl, 2-fluorophenyl, 2-chlorophenyl, 2-trifluoromethoxyphenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 3-chloro-4-fluorophenyl, 3,4-difluorophenyl, 3-fluoro-6-trifluoromethylphenyl and 3,4,6-trifluorophenyl; R₇ is selected from H, (C₁-C₆)alkyl, cyclo(C₅-C₆)alkyl, halo(C₁-C₆)alkyl and COR₉; R₈ is (C₁-C₆)alkyl, cyclo(C₅-C₆)alkyl, halo(C₁-C₁₂)alkyl, 1-naphthyl, 2-naphthyl, phenyl, 4-methylphenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-fluorophenyl, 4-chlorophenyl, 4-trifluoromethylphenyl, 4-bromophenyl, 4-chlorophenyl, 3-fluorophenyl, 4-trifluoromethoxyphenyl, 4-cyanophenyl, 3-(1,3-dioxolan-2-yl)phenyl, 2-fluorophenyl, 2-chlorophenyl, 2-trifluoromethoxyphenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 3-chloro-4-fluorophenyl, 3,4-difluorophenyl, 3-fluoro-5trifluoromethylphenyl and 3,4,5-trifluorophenyl; R₉ is selected from H, (C₁-C₆)alkyl, (C₂-C₆)alkenyl, cyclo(C₅C₆)alkyl and halo(C₁-C₆)alkyl; R₁₀ is selected from H, chloro, NH₂, (C₁-C₆)alkyl, halo(C₁-C₆)alkyl, CN, CO₂(C₁-C₆)alkyl, CONH(C₁-C₆)alkyl, CON((C₁-C₆)alkyl)₂, CH₂CN, CH₂CH═CH₂, CH₂C≡CH, CH₂CO₂(C₁-C₆)alkyl, CH₂OCH₃ and CH₂-1,2,4-triazole; R₁₁ is H, CN, (C₁-C₆)alkyl, halo(C₁-C₆)alkyl and CO₂(C₁-C₆)alkyl; R₁₂ is selected from H, (C₁-C₈)alkyl, CO₂(C₁-C₆)alkyl, CON((C₁-C₆)alkyl)₂, O(C₁-C₆)alkyl, S(C₁-C₆)alkyl, SO₂(C₁-C₆)alkyl, SO₂N((C₁-C₆)alkyl)₂ and N(C₁-C₈)alkyl)₂; R₁₃ is H, (C₁-C₆)alkyl, aryl or aryl(C₁-C₄)alkyl where the aryl group is naphthyl or phenyl; A is N; B is N; Z is O, CH(R₃), CO, CS, CONR₁₂ or CSNR₁₂; X is selected from O, S, NH, CO₂, OCH(R₆)CO₂, SCH(R₆)CO₂, CH═C(Cl)CO₂, CH₂CH(Cl)CO₂, CONH, OCH(R₆)CONH, SCH(R₆)CONH, CH═C(Cl)CONH and CH₃CH(Cl)CONH when Z is CH(R₃); X is selected from CO, OCH(R₆)CO, SCH(R₆)CO, CH═C(Cl)CO and CH₂CH(Cl)CO when Z is O; X is selected from O, S, CO, OCH(R₆), CH═C(Cl), CH₂CH(Cl), CONH OCH(R₆)CONH, SCH(R₆)CONH, CH═C(Cl)CONH, CH₂CH(Cl)CONH and NR₁₂ when Z is CO, CS, CONR₁₂ or CSNR₁₂; Q is selected from Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q14, Q15 and Q16; or the agronomically acceptable salts thereof selected from those formed from hydrochloric acid, acetic acid, phosphoric acid and oxalic acid.
 5. A herbicidal composition comprising a compound as in claim 1, 2, 3 or 4 and an agronomically acceptable carrier.
 6. The composition of claim 5 which contains from about 0.1% to 99% by weight of said compound.
 7. The composition of claim 6 further comprising a second pesticide or a fertilizer.
 8. A method of controlling a weed comprising applying a herbicidally effective amount of a composition of claim 5 and an agronomically acceptable carrier to the weed, to the locus of the weed or to the growth medium of said weed. 